A Lewis acid mediated stereoselective removal of an anomeric urea substituent

Synlett

Volumn , Issue 6, 2003, Pages 791-796

  Berry, Craig R ^a   Rameshkumar, C ^a   Tracey, Michael R ^a   Wei, Lin Li ^a   Hsung, Richard P ^a  

^a University of Minnesota   (United States)

Author keywords

C glycoside derivatives; Lewis acid

Indexed keywords

ALKENE; GLYCOSIDE; HETEROCYCLIC COMPOUND; LEWIS ACID; UREA DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; DIASTEREOISOMER; STEREOCHEMISTRY; SYNTHESIS; TEMPERATURE;

EID: 0038731303     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-38747     Document Type: Article

References (75)

1. A Recipient of 2001 Camille Dreyfus Teacher-Scholar Award. Author names are alphabetically ordered.
2. For reviews on allenes see: (a) Saalfrank, R. W.; Lurz, C. J. In Houben-Weyl, Methoden der organischen Chemie; Kropf, H.; Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1993, 3093. (b) Schuster, H. E.; Coppola, G. M. Allenes in Organic Synthesis; John Wiley and Sons: New York, 1984. (c) For documentations of earlier allenamides, see: Dickinson, W. B.; Lang, P. C. Tetrahedron Lett. 1967, 8, 3035. (d) Corbel, B.; Paugam, J.-P.; Dreux, M.; Savignac, P. Tetrahedron Lett. 1976, 17, 835. (e) Balasubramanian, K. K.; Venugopalan, B. Tetrahedron Lett. 1974, 15, 2643. (f) Overman, L. E.; Marlowe, C. K.; Clizbe, L. A. Tetrahedron Lett. 1979, 599. (g) Reisch, J.; Salehi-Artimani, R. A. J. Heterocycl. Chem. 1989, 26, 1803.
3. For reviews on allenes see: (a) Saalfrank, R. W.; Lurz, C. J. In Houben-Weyl, Methoden der organischen Chemie; Kropf, H.; Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1993, 3093. (b) Schuster, H. E.; Coppola, G. M. Allenes in Organic Synthesis; John Wiley and Sons: New York, 1984. (c) For documentations of earlier allenamides, see: Dickinson, W. B.; Lang, P. C. Tetrahedron Lett. 1967, 8, 3035. (d) Corbel, B.; Paugam, J.-P.; Dreux, M.; Savignac, P. Tetrahedron Lett. 1976, 17, 835. (e) Balasubramanian, K. K.; Venugopalan, B. Tetrahedron Lett. 1974, 15, 2643. (f) Overman, L. E.; Marlowe, C. K.; Clizbe, L. A. Tetrahedron Lett. 1979, 599. (g) Reisch, J.; Salehi-Artimani, R. A. J. Heterocycl. Chem. 1989, 26, 1803.
4. For reviews on allenes see: (a) Saalfrank, R. W.; Lurz, C. J. In Houben-Weyl, Methoden der organischen Chemie; Kropf, H.; Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1993, 3093. (b) Schuster, H. E.; Coppola, G. M. Allenes in Organic Synthesis; John Wiley and Sons: New York, 1984. (c) For documentations of earlier allenamides, see: Dickinson, W. B.; Lang, P. C. Tetrahedron Lett. 1967, 8, 3035. (d) Corbel, B.; Paugam, J.-P.; Dreux, M.; Savignac, P. Tetrahedron Lett. 1976, 17, 835. (e) Balasubramanian, K. K.; Venugopalan, B. Tetrahedron Lett. 1974, 15, 2643. (f) Overman, L. E.; Marlowe, C. K.; Clizbe, L. A. Tetrahedron Lett. 1979, 599. (g) Reisch, J.; Salehi-Artimani, R. A. J. Heterocycl. Chem. 1989, 26, 1803.
5. For reviews on allenes see: (a) Saalfrank, R. W.; Lurz, C. J. In Houben-Weyl, Methoden der organischen Chemie; Kropf, H.; Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1993, 3093. (b) Schuster, H. E.; Coppola, G. M. Allenes in Organic Synthesis; John Wiley and Sons: New York, 1984. (c) For documentations of earlier allenamides, see: Dickinson, W. B.; Lang, P. C. Tetrahedron Lett. 1967, 8, 3035. (d) Corbel, B.; Paugam, J.-P.; Dreux, M.; Savignac, P. Tetrahedron Lett. 1976, 17, 835. (e) Balasubramanian, K. K.; Venugopalan, B. Tetrahedron Lett. 1974, 15, 2643. (f) Overman, L. E.; Marlowe, C. K.; Clizbe, L. A. Tetrahedron Lett. 1979, 599. (g) Reisch, J.; Salehi-Artimani, R. A. J. Heterocycl. Chem. 1989, 26, 1803.
6. For reviews on allenes see: (a) Saalfrank, R. W.; Lurz, C. J. In Houben-Weyl, Methoden der organischen Chemie; Kropf, H.; Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1993, 3093. (b) Schuster, H. E.; Coppola, G. M. Allenes in Organic Synthesis; John Wiley and Sons: New York, 1984. (c) For documentations of earlier allenamides, see: Dickinson, W. B.; Lang, P. C. Tetrahedron Lett. 1967, 8, 3035. (d) Corbel, B.; Paugam, J.-P.; Dreux, M.; Savignac, P. Tetrahedron Lett. 1976, 17, 835. (e) Balasubramanian, K. K.; Venugopalan, B. Tetrahedron Lett. 1974, 15, 2643. (f) Overman, L. E.; Marlowe, C. K.; Clizbe, L. A. Tetrahedron Lett. 1979, 599. (g) Reisch, J.; Salehi-Artimani, R. A. J. Heterocycl. Chem. 1989, 26, 1803.
7. For reviews on allenes see: (a) Saalfrank, R. W.; Lurz, C. J. In Houben-Weyl, Methoden der organischen Chemie; Kropf, H.; Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1993, 3093. (b) Schuster, H. E.; Coppola, G. M. Allenes in Organic Synthesis; John Wiley and Sons: New York, 1984. (c) For documentations of earlier allenamides, see: Dickinson, W. B.; Lang, P. C. Tetrahedron Lett. 1967, 8, 3035. (d) Corbel, B.; Paugam, J.-P.; Dreux, M.; Savignac, P. Tetrahedron Lett. 1976, 17, 835. (e) Balasubramanian, K. K.; Venugopalan, B. Tetrahedron Lett. 1974, 15, 2643. (f) Overman, L. E.; Marlowe, C. K.; Clizbe, L. A. Tetrahedron Lett. 1979, 599. (g) Reisch, J.; Salehi-Artimani, R. A. J. Heterocycl. Chem. 1989, 26, 1803.
8. For reviews on allenes see: (a) Saalfrank, R. W.; Lurz, C. J. In Houben-Weyl, Methoden der organischen Chemie; Kropf, H.; Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1993, 3093. (b) Schuster, H. E.; Coppola, G. M. Allenes in Organic Synthesis; John Wiley and Sons: New York, 1984. (c) For documentations of earlier allenamides, see: Dickinson, W. B.; Lang, P. C. Tetrahedron Lett. 1967, 8, 3035. (d) Corbel, B.; Paugam, J.-P.; Dreux, M.; Savignac, P. Tetrahedron Lett. 1976, 17, 835. (e) Balasubramanian, K. K.; Venugopalan, B. Tetrahedron Lett. 1974, 15, 2643. (f) Overman, L. E.; Marlowe, C. K.; Clizbe, L. A. Tetrahedron Lett. 1979, 599. (g) Reisch, J.; Salehi-Artimani, R. A. J. Heterocycl. Chem. 1989, 26, 1803.
9. For recent chemistry using allenamides, see: (a) Gaul, C.; Seebach, D. Helv. Chim. Acta 2002, 85, 963. (b) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 1499. (c) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2001, 42, 4869. (d) Kinderman, S. S.; van Maarseveen, J. H.; Schoemaker, H. E.; Hiemstra, H.; Rutjes, F. P. T. Org. Lett. 2001, 3, 2045. (e) van Boxtel, L. J.; Korbe, S.; Noltemeyer, M.; de Meijere, A. Eur. J. Org. Chem. 2001, 2283. (f) Grigg, R.; Köppen, I.; Rasparini, M.; Sridharan, V. Chem. Commun. 2001, 964. (g) Gardiner, M.; Grigg, R.; Sridharan, V.; Vicker, N. Tetrahedron Lett. 1998, 39, 435. (h) Grigg, R.; Sansano, J. M.; Santhakumar, V.; Sridharan, V.; Thangavelanthum, R.; Thornton-Pett, M.; Wilson, D. Tetrahedron 1997, 53, 11803. (i) Grigg, R.; Loganathan, V.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S.; Worakun, T. Tetrahedron 1996, 52, 11479. (j) Griggs, R.; Sansano, J. M. Tetrahedron 1996, 52, 13441. (k) Grigg, R.; Sridharan, V.; Xu, L.-H. J. Chem. Soc., Chem. Commun. 1995, 1903. (l) Kimura, M.; Horino, Y.; Wakamiya, Y.; Okajima, T.; Tamaru, Y. J. Am. Chem. Soc. 1997, 119, 10869. (m) Kimura, M.; Wakamiya, Y.; Horino, Y.; Tamaru, Y. Tetrahedron Lett. 1997, 38, 3963. (n) Horino, Y.; Kimura, M.; Wakamiya, Y.; Okajima, T.; Tamaru, Y. Angew. Chem. Int. Ed. 1999, 38, 121. (o) Noguchi, M.; Okada, H.; Wantanabe, M.; Okuda, K.; Nakamura, O. Tetrahedron 1996, 52, 6581. (p) Gericke, R.; Lues, I. Tetrahedron Lett. 1992, 33, 1871. (q) Tanaka, H.; Kameyama, Y.; Sumida, S.; Yamada, T.; Tokumaru, Y.; Shiroi, T.; Sasaoka, M.; Taniguchi, M.; Torri, S. Synlett 1991, 888. (r) Farina, V.; Kant, J. Tetrahedron Lett. 1992, 33, 3563. (s) Farina, V.; Kant, J. Tetrahedron Lett. 1992, 33, 3559. (t) Broggini, G.; Bruché, L.; Zecchi, G. J. Chem. Soc., Perkin Trans. 1 1990, 533. (u) Nilsson, B. M.; Hacksell, U. J. Heterocycl. Chem. 1989, 26, 269. (v) Jones, B. C. N. M.; Silverton, J. V.; Simons, C.; Megati, S.; Nishimura, H.; Maeda, Y.; Mitsuya, H.; Zemlicka, J. J. Med. Chem. 1995, 38, 1397. (w) Rádl, S.; Kovárová, L. Collect. Czech. Chem. Commun. 1991, 56, 2413. (x) For an account on living polymerization of allenamides, see: Takagi, K.; Tomita, I.; Endo, T. Macromolecules 1998, 31, 6741.
10. For recent chemistry using allenamides, see: (a) Gaul, C.; Seebach, D. Helv. Chim. Acta 2002, 85, 963. (b) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 1499. (c) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2001, 42, 4869. (d) Kinderman, S. S.; van Maarseveen, J. H.; Schoemaker, H. E.; Hiemstra, H.; Rutjes, F. P. T. Org. Lett. 2001, 3, 2045. (e) van Boxtel, L. J.; Korbe, S.; Noltemeyer, M.; de Meijere, A. Eur. J. Org. Chem. 2001, 2283. (f) Grigg, R.; Köppen, I.; Rasparini, M.; Sridharan, V. Chem. Commun. 2001, 964. (g) Gardiner, M.; Grigg, R.; Sridharan, V.; Vicker, N. Tetrahedron Lett. 1998, 39, 435. (h) Grigg, R.; Sansano, J. M.; Santhakumar, V.; Sridharan, V.; Thangavelanthum, R.; Thornton-Pett, M.; Wilson, D. Tetrahedron 1997, 53, 11803. (i) Grigg, R.; Loganathan, V.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S.; Worakun, T. Tetrahedron 1996, 52, 11479. (j) Griggs, R.; Sansano, J. M. Tetrahedron 1996, 52, 13441. (k) Grigg, R.; Sridharan, V.; Xu, L.-H. J. Chem. Soc., Chem. Commun. 1995, 1903. (l) Kimura, M.; Horino, Y.; Wakamiya, Y.; Okajima, T.; Tamaru, Y. J. Am. Chem. Soc. 1997, 119, 10869. (m) Kimura, M.; Wakamiya, Y.; Horino, Y.; Tamaru, Y. Tetrahedron Lett. 1997, 38, 3963. (n) Horino, Y.; Kimura, M.; Wakamiya, Y.; Okajima, T.; Tamaru, Y. Angew. Chem. Int. Ed. 1999, 38, 121. (o) Noguchi, M.; Okada, H.; Wantanabe, M.; Okuda, K.; Nakamura, O. Tetrahedron 1996, 52, 6581. (p) Gericke, R.; Lues, I. Tetrahedron Lett. 1992, 33, 1871. (q) Tanaka, H.; Kameyama, Y.; Sumida, S.; Yamada, T.; Tokumaru, Y.; Shiroi, T.; Sasaoka, M.; Taniguchi, M.; Torri, S. Synlett 1991, 888. (r) Farina, V.; Kant, J. Tetrahedron Lett. 1992, 33, 3563. (s) Farina, V.; Kant, J. Tetrahedron Lett. 1992, 33, 3559. (t) Broggini, G.; Bruché, L.; Zecchi, G. J. Chem. Soc., Perkin Trans. 1 1990, 533. (u) Nilsson, B. M.; Hacksell, U. J. Heterocycl. Chem. 1989, 26, 269. (v) Jones, B. C. N. M.; Silverton, J. V.; Simons, C.; Megati, S.; Nishimura, H.; Maeda, Y.; Mitsuya, H.; Zemlicka, J. J. Med. Chem. 1995, 38, 1397. (w) Rádl, S.; Kovárová, L. Collect. Czech. Chem. Commun. 1991, 56, 2413. (x) For an account on living polymerization of allenamides, see: Takagi, K.; Tomita, I.; Endo, T. Macromolecules 1998, 31, 6741.
11. For recent chemistry using allenamides, see: (a) Gaul, C.; Seebach, D. Helv. Chim. Acta 2002, 85, 963. (b) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 1499. (c) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2001, 42, 4869. (d) Kinderman, S. S.; van Maarseveen, J. H.; Schoemaker, H. E.; Hiemstra, H.; Rutjes, F. P. T. Org. Lett. 2001, 3, 2045. (e) van Boxtel, L. J.; Korbe, S.; Noltemeyer, M.; de Meijere, A. Eur. J. Org. Chem. 2001, 2283. (f) Grigg, R.; Köppen, I.; Rasparini, M.; Sridharan, V. Chem. Commun. 2001, 964. (g) Gardiner, M.; Grigg, R.; Sridharan, V.; Vicker, N. Tetrahedron Lett. 1998, 39, 435. (h) Grigg, R.; Sansano, J. M.; Santhakumar, V.; Sridharan, V.; Thangavelanthum, R.; Thornton-Pett, M.; Wilson, D. Tetrahedron 1997, 53, 11803. (i) Grigg, R.; Loganathan, V.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S.; Worakun, T. Tetrahedron 1996, 52, 11479. (j) Griggs, R.; Sansano, J. M. Tetrahedron 1996, 52, 13441. (k) Grigg, R.; Sridharan, V.; Xu, L.-H. J. Chem. Soc., Chem. Commun. 1995, 1903. (l) Kimura, M.; Horino, Y.; Wakamiya, Y.; Okajima, T.; Tamaru, Y. J. Am. Chem. Soc. 1997, 119, 10869. (m) Kimura, M.; Wakamiya, Y.; Horino, Y.; Tamaru, Y. Tetrahedron Lett. 1997, 38, 3963. (n) Horino, Y.; Kimura, M.; Wakamiya, Y.; Okajima, T.; Tamaru, Y. Angew. Chem. Int. Ed. 1999, 38, 121. (o) Noguchi, M.; Okada, H.; Wantanabe, M.; Okuda, K.; Nakamura, O. Tetrahedron 1996, 52, 6581. (p) Gericke, R.; Lues, I. Tetrahedron Lett. 1992, 33, 1871. (q) Tanaka, H.; Kameyama, Y.; Sumida, S.; Yamada, T.; Tokumaru, Y.; Shiroi, T.; Sasaoka, M.; Taniguchi, M.; Torri, S. Synlett 1991, 888. (r) Farina, V.; Kant, J. Tetrahedron Lett. 1992, 33, 3563. (s) Farina, V.; Kant, J. Tetrahedron Lett. 1992, 33, 3559. (t) Broggini, G.; Bruché, L.; Zecchi, G. J. Chem. Soc., Perkin Trans. 1 1990, 533. (u) Nilsson, B. M.; Hacksell, U. J. Heterocycl. Chem. 1989, 26, 269. (v) Jones, B. C. N. M.; Silverton, J. V.; Simons, C.; Megati, S.; Nishimura, H.; Maeda, Y.; Mitsuya, H.; Zemlicka, J. J. Med. Chem. 1995, 38, 1397. (w) Rádl, S.; Kovárová, L. Collect. Czech. Chem. Commun. 1991, 56, 2413. (x) For an account on living polymerization of allenamides, see: Takagi, K.; Tomita, I.; Endo, T. Macromolecules 1998, 31, 6741.
12. For recent chemistry using allenamides, see: (a) Gaul, C.; Seebach, D. Helv. Chim. Acta 2002, 85, 963. (b) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 1499. (c) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2001, 42, 4869. (d) Kinderman, S. S.; van Maarseveen, J. H.; Schoemaker, H. E.; Hiemstra, H.; Rutjes, F. P. T. Org. Lett. 2001, 3, 2045. (e) van Boxtel, L. J.; Korbe, S.; Noltemeyer, M.; de Meijere, A. Eur. J. Org. Chem. 2001, 2283. (f) Grigg, R.; Köppen, I.; Rasparini, M.; Sridharan, V. Chem. Commun. 2001, 964. (g) Gardiner, M.; Grigg, R.; Sridharan, V.; Vicker, N. Tetrahedron Lett. 1998, 39, 435. (h) Grigg, R.; Sansano, J. M.; Santhakumar, V.; Sridharan, V.; Thangavelanthum, R.; Thornton-Pett, M.; Wilson, D. Tetrahedron 1997, 53, 11803. (i) Grigg, R.; Loganathan, V.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S.; Worakun, T. Tetrahedron 1996, 52, 11479. (j) Griggs, R.; Sansano, J. M. Tetrahedron 1996, 52, 13441. (k) Grigg, R.; Sridharan, V.; Xu, L.-H. J. Chem. Soc., Chem. Commun. 1995, 1903. (l) Kimura, M.; Horino, Y.; Wakamiya, Y.; Okajima, T.; Tamaru, Y. J. Am. Chem. Soc. 1997, 119, 10869. (m) Kimura, M.; Wakamiya, Y.; Horino, Y.; Tamaru, Y. Tetrahedron Lett. 1997, 38, 3963. (n) Horino, Y.; Kimura, M.; Wakamiya, Y.; Okajima, T.; Tamaru, Y. Angew. Chem. Int. Ed. 1999, 38, 121. (o) Noguchi, M.; Okada, H.; Wantanabe, M.; Okuda, K.; Nakamura, O. Tetrahedron 1996, 52, 6581. (p) Gericke, R.; Lues, I. Tetrahedron Lett. 1992, 33, 1871. (q) Tanaka, H.; Kameyama, Y.; Sumida, S.; Yamada, T.; Tokumaru, Y.; Shiroi, T.; Sasaoka, M.; Taniguchi, M.; Torri, S. Synlett 1991, 888. (r) Farina, V.; Kant, J. Tetrahedron Lett. 1992, 33, 3563. (s) Farina, V.; Kant, J. Tetrahedron Lett. 1992, 33, 3559. (t) Broggini, G.; Bruché, L.; Zecchi, G. J. Chem. Soc., Perkin Trans. 1 1990, 533. (u) Nilsson, B. M.; Hacksell, U. J. Heterocycl. Chem. 1989, 26, 269. (v) Jones, B. C. N. M.; Silverton, J. V.; Simons, C.; Megati, S.; Nishimura, H.; Maeda, Y.; Mitsuya, H.; Zemlicka, J. J. Med. Chem. 1995, 38, 1397. (w) Rádl, S.; Kovárová, L. Collect. Czech. Chem. Commun. 1991, 56, 2413. (x) For an account on living polymerization of allenamides, see: Takagi, K.; Tomita, I.; Endo, T. Macromolecules 1998, 31, 6741.
13. For recent chemistry using allenamides, see: (a) Gaul, C.; Seebach, D. Helv. Chim. Acta 2002, 85, 963. (b) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 1499. (c) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2001, 42, 4869. (d) Kinderman, S. S.; van Maarseveen, J. H.; Schoemaker, H. E.; Hiemstra, H.; Rutjes, F. P. T. Org. Lett. 2001, 3, 2045. (e) van Boxtel, L. J.; Korbe, S.; Noltemeyer, M.; de Meijere, A. Eur. J. Org. Chem. 2001, 2283. (f) Grigg, R.; Köppen, I.; Rasparini, M.; Sridharan, V. Chem. Commun. 2001, 964. (g) Gardiner, M.; Grigg, R.; Sridharan, V.; Vicker, N. Tetrahedron Lett. 1998, 39, 435. (h) Grigg, R.; Sansano, J. M.; Santhakumar, V.; Sridharan, V.; Thangavelanthum, R.; Thornton-Pett, M.; Wilson, D. Tetrahedron 1997, 53, 11803. (i) Grigg, R.; Loganathan, V.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S.; Worakun, T. Tetrahedron 1996, 52, 11479. (j) Griggs, R.; Sansano, J. M. Tetrahedron 1996, 52, 13441. (k) Grigg, R.; Sridharan, V.; Xu, L.-H. J. Chem. Soc., Chem. Commun. 1995, 1903. (l) Kimura, M.; Horino, Y.; Wakamiya, Y.; Okajima, T.; Tamaru, Y. J. Am. Chem. Soc. 1997, 119, 10869. (m) Kimura, M.; Wakamiya, Y.; Horino, Y.; Tamaru, Y. Tetrahedron Lett. 1997, 38, 3963. (n) Horino, Y.; Kimura, M.; Wakamiya, Y.; Okajima, T.; Tamaru, Y. Angew. Chem. Int. Ed. 1999, 38, 121. (o) Noguchi, M.; Okada, H.; Wantanabe, M.; Okuda, K.; Nakamura, O. Tetrahedron 1996, 52, 6581. (p) Gericke, R.; Lues, I. Tetrahedron Lett. 1992, 33, 1871. (q) Tanaka, H.; Kameyama, Y.; Sumida, S.; Yamada, T.; Tokumaru, Y.; Shiroi, T.; Sasaoka, M.; Taniguchi, M.; Torri, S. Synlett 1991, 888. (r) Farina, V.; Kant, J. Tetrahedron Lett. 1992, 33, 3563. (s) Farina, V.; Kant, J. Tetrahedron Lett. 1992, 33, 3559. (t) Broggini, G.; Bruché, L.; Zecchi, G. J. Chem. Soc., Perkin Trans. 1 1990, 533. (u) Nilsson, B. M.; Hacksell, U. J. Heterocycl. Chem. 1989, 26, 269. (v) Jones, B. C. N. M.; Silverton, J. V.; Simons, C.; Megati, S.; Nishimura, H.; Maeda, Y.; Mitsuya, H.; Zemlicka, J. J. Med. Chem. 1995, 38, 1397. (w) Rádl, S.; Kovárová, L. Collect. Czech. Chem. Commun. 1991, 56, 2413. (x) For an account on living polymerization of allenamides, see: Takagi, K.; Tomita, I.; Endo, T. Macromolecules 1998, 31, 6741.
14. For recent chemistry using allenamides, see: (a) Gaul, C.; Seebach, D. Helv. Chim. Acta 2002, 85, 963. (b) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 1499. (c) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2001, 42, 4869. (d) Kinderman, S. S.; van Maarseveen, J. H.; Schoemaker, H. E.; Hiemstra, H.; Rutjes, F. P. T. Org. Lett. 2001, 3, 2045. (e) van Boxtel, L. J.; Korbe, S.; Noltemeyer, M.; de Meijere, A. Eur. J. Org. Chem. 2001, 2283. (f) Grigg, R.; Köppen, I.; Rasparini, M.; Sridharan, V. Chem. Commun. 2001, 964. (g) Gardiner, M.; Grigg, R.; Sridharan, V.; Vicker, N. Tetrahedron Lett. 1998, 39, 435. (h) Grigg, R.; Sansano, J. M.; Santhakumar, V.; Sridharan, V.; Thangavelanthum, R.; Thornton-Pett, M.; Wilson, D. Tetrahedron 1997, 53, 11803. (i) Grigg, R.; Loganathan, V.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S.; Worakun, T. Tetrahedron 1996, 52, 11479. (j) Griggs, R.; Sansano, J. M. Tetrahedron 1996, 52, 13441. (k) Grigg, R.; Sridharan, V.; Xu, L.-H. J. Chem. Soc., Chem. Commun. 1995, 1903. (l) Kimura, M.; Horino, Y.; Wakamiya, Y.; Okajima, T.; Tamaru, Y. J. Am. Chem. Soc. 1997, 119, 10869. (m) Kimura, M.; Wakamiya, Y.; Horino, Y.; Tamaru, Y. Tetrahedron Lett. 1997, 38, 3963. (n) Horino, Y.; Kimura, M.; Wakamiya, Y.; Okajima, T.; Tamaru, Y. Angew. Chem. Int. Ed. 1999, 38, 121. (o) Noguchi, M.; Okada, H.; Wantanabe, M.; Okuda, K.; Nakamura, O. Tetrahedron 1996, 52, 6581. (p) Gericke, R.; Lues, I. Tetrahedron Lett. 1992, 33, 1871. (q) Tanaka, H.; Kameyama, Y.; Sumida, S.; Yamada, T.; Tokumaru, Y.; Shiroi, T.; Sasaoka, M.; Taniguchi, M.; Torri, S. Synlett 1991, 888. (r) Farina, V.; Kant, J. Tetrahedron Lett. 1992, 33, 3563. (s) Farina, V.; Kant, J. Tetrahedron Lett. 1992, 33, 3559. (t) Broggini, G.; Bruché, L.; Zecchi, G. J. Chem. Soc., Perkin Trans. 1 1990, 533. (u) Nilsson, B. M.; Hacksell, U. J. Heterocycl. Chem. 1989, 26, 269. (v) Jones, B. C. N. M.; Silverton, J. V.; Simons, C.; Megati, S.; Nishimura, H.; Maeda, Y.; Mitsuya, H.; Zemlicka, J. J. Med. Chem. 1995, 38, 1397. (w) Rádl, S.; Kovárová, L. Collect. Czech. Chem. Commun. 1991, 56, 2413. (x) For an account on living polymerization of allenamides, see: Takagi, K.; Tomita, I.; Endo, T. Macromolecules 1998, 31, 6741.
15. For recent chemistry using allenamides, see: (a) Gaul, C.; Seebach, D. Helv. Chim. Acta 2002, 85, 963. (b) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 1499. (c) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2001, 42, 4869. (d) Kinderman, S. S.; van Maarseveen, J. H.; Schoemaker, H. E.; Hiemstra, H.; Rutjes, F. P. T. Org. Lett. 2001, 3, 2045. (e) van Boxtel, L. J.; Korbe, S.; Noltemeyer, M.; de Meijere, A. Eur. J. Org. Chem. 2001, 2283. (f) Grigg, R.; Köppen, I.; Rasparini, M.; Sridharan, V. Chem. Commun. 2001, 964. (g) Gardiner, M.; Grigg, R.; Sridharan, V.; Vicker, N. Tetrahedron Lett. 1998, 39, 435. (h) Grigg, R.; Sansano, J. M.; Santhakumar, V.; Sridharan, V.; Thangavelanthum, R.; Thornton-Pett, M.; Wilson, D. Tetrahedron 1997, 53, 11803. (i) Grigg, R.; Loganathan, V.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S.; Worakun, T. Tetrahedron 1996, 52, 11479. (j) Griggs, R.; Sansano, J. M. Tetrahedron 1996, 52, 13441. (k) Grigg, R.; Sridharan, V.; Xu, L.-H. J. Chem. Soc., Chem. Commun. 1995, 1903. (l) Kimura, M.; Horino, Y.; Wakamiya, Y.; Okajima, T.; Tamaru, Y. J. Am. Chem. Soc. 1997, 119, 10869. (m) Kimura, M.; Wakamiya, Y.; Horino, Y.; Tamaru, Y. Tetrahedron Lett. 1997, 38, 3963. (n) Horino, Y.; Kimura, M.; Wakamiya, Y.; Okajima, T.; Tamaru, Y. Angew. Chem. Int. Ed. 1999, 38, 121. (o) Noguchi, M.; Okada, H.; Wantanabe, M.; Okuda, K.; Nakamura, O. Tetrahedron 1996, 52, 6581. (p) Gericke, R.; Lues, I. Tetrahedron Lett. 1992, 33, 1871. (q) Tanaka, H.; Kameyama, Y.; Sumida, S.; Yamada, T.; Tokumaru, Y.; Shiroi, T.; Sasaoka, M.; Taniguchi, M.; Torri, S. Synlett 1991, 888. (r) Farina, V.; Kant, J. Tetrahedron Lett. 1992, 33, 3563. (s) Farina, V.; Kant, J. Tetrahedron Lett. 1992, 33, 3559. (t) Broggini, G.; Bruché, L.; Zecchi, G. J. Chem. Soc., Perkin Trans. 1 1990, 533. (u) Nilsson, B. M.; Hacksell, U. J. Heterocycl. Chem. 1989, 26, 269. (v) Jones, B. C. N. M.; Silverton, J. V.; Simons, C.; Megati, S.; Nishimura, H.; Maeda, Y.; Mitsuya, H.; Zemlicka, J. J. Med. Chem. 1995, 38, 1397. (w) Rádl, S.; Kovárová, L. Collect. Czech. Chem. Commun. 1991, 56, 2413. (x) For an account on living polymerization of allenamides, see: Takagi, K.; Tomita, I.; Endo, T. Macromolecules 1998, 31, 6741.
16. For recent chemistry using allenamides, see: (a) Gaul, C.; Seebach, D. Helv. Chim. Acta 2002, 85, 963. (b) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 1499. (c) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2001, 42, 4869. (d) Kinderman, S. S.; van Maarseveen, J. H.; Schoemaker, H. E.; Hiemstra, H.; Rutjes, F. P. T. Org. Lett. 2001, 3, 2045. (e) van Boxtel, L. J.; Korbe, S.; Noltemeyer, M.; de Meijere, A. Eur. J. Org. Chem. 2001, 2283. (f) Grigg, R.; Köppen, I.; Rasparini, M.; Sridharan, V. Chem. Commun. 2001, 964. (g) Gardiner, M.; Grigg, R.; Sridharan, V.; Vicker, N. Tetrahedron Lett. 1998, 39, 435. (h) Grigg, R.; Sansano, J. M.; Santhakumar, V.; Sridharan, V.; Thangavelanthum, R.; Thornton-Pett, M.; Wilson, D. Tetrahedron 1997, 53, 11803. (i) Grigg, R.; Loganathan, V.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S.; Worakun, T. Tetrahedron 1996, 52, 11479. (j) Griggs, R.; Sansano, J. M. Tetrahedron 1996, 52, 13441. (k) Grigg, R.; Sridharan, V.; Xu, L.-H. J. Chem. Soc., Chem. Commun. 1995, 1903. (l) Kimura, M.; Horino, Y.; Wakamiya, Y.; Okajima, T.; Tamaru, Y. J. Am. Chem. Soc. 1997, 119, 10869. (m) Kimura, M.; Wakamiya, Y.; Horino, Y.; Tamaru, Y. Tetrahedron Lett. 1997, 38, 3963. (n) Horino, Y.; Kimura, M.; Wakamiya, Y.; Okajima, T.; Tamaru, Y. Angew. Chem. Int. Ed. 1999, 38, 121. (o) Noguchi, M.; Okada, H.; Wantanabe, M.; Okuda, K.; Nakamura, O. Tetrahedron 1996, 52, 6581. (p) Gericke, R.; Lues, I. Tetrahedron Lett. 1992, 33, 1871. (q) Tanaka, H.; Kameyama, Y.; Sumida, S.; Yamada, T.; Tokumaru, Y.; Shiroi, T.; Sasaoka, M.; Taniguchi, M.; Torri, S. Synlett 1991, 888. (r) Farina, V.; Kant, J. Tetrahedron Lett. 1992, 33, 3563. (s) Farina, V.; Kant, J. Tetrahedron Lett. 1992, 33, 3559. (t) Broggini, G.; Bruché, L.; Zecchi, G. J. Chem. Soc., Perkin Trans. 1 1990, 533. (u) Nilsson, B. M.; Hacksell, U. J. Heterocycl. Chem. 1989, 26, 269. (v) Jones, B. C. N. M.; Silverton, J. V.; Simons, C.; Megati, S.; Nishimura, H.; Maeda, Y.; Mitsuya, H.; Zemlicka, J. J. Med. Chem. 1995, 38, 1397. (w) Rádl, S.; Kovárová, L. Collect. Czech. Chem. Commun. 1991, 56, 2413. (x) For an account on living polymerization of allenamides, see: Takagi, K.; Tomita, I.; Endo, T. Macromolecules 1998, 31, 6741.
17. For recent chemistry using allenamides, see: (a) Gaul, C.; Seebach, D. Helv. Chim. Acta 2002, 85, 963. (b) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 1499. (c) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2001, 42, 4869. (d) Kinderman, S. S.; van Maarseveen, J. H.; Schoemaker, H. E.; Hiemstra, H.; Rutjes, F. P. T. Org. Lett. 2001, 3, 2045. (e) van Boxtel, L. J.; Korbe, S.; Noltemeyer, M.; de Meijere, A. Eur. J. Org. Chem. 2001, 2283. (f) Grigg, R.; Köppen, I.; Rasparini, M.; Sridharan, V. Chem. Commun. 2001, 964. (g) Gardiner, M.; Grigg, R.; Sridharan, V.; Vicker, N. Tetrahedron Lett. 1998, 39, 435. (h) Grigg, R.; Sansano, J. M.; Santhakumar, V.; Sridharan, V.; Thangavelanthum, R.; Thornton-Pett, M.; Wilson, D. Tetrahedron 1997, 53, 11803. (i) Grigg, R.; Loganathan, V.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S.; Worakun, T. Tetrahedron 1996, 52, 11479. (j) Griggs, R.; Sansano, J. M. Tetrahedron 1996, 52, 13441. (k) Grigg, R.; Sridharan, V.; Xu, L.-H. J. Chem. Soc., Chem. Commun. 1995, 1903. (l) Kimura, M.; Horino, Y.; Wakamiya, Y.; Okajima, T.; Tamaru, Y. J. Am. Chem. Soc. 1997, 119, 10869. (m) Kimura, M.; Wakamiya, Y.; Horino, Y.; Tamaru, Y. Tetrahedron Lett. 1997, 38, 3963. (n) Horino, Y.; Kimura, M.; Wakamiya, Y.; Okajima, T.; Tamaru, Y. Angew. Chem. Int. Ed. 1999, 38, 121. (o) Noguchi, M.; Okada, H.; Wantanabe, M.; Okuda, K.; Nakamura, O. Tetrahedron 1996, 52, 6581. (p) Gericke, R.; Lues, I. Tetrahedron Lett. 1992, 33, 1871. (q) Tanaka, H.; Kameyama, Y.; Sumida, S.; Yamada, T.; Tokumaru, Y.; Shiroi, T.; Sasaoka, M.; Taniguchi, M.; Torri, S. Synlett 1991, 888. (r) Farina, V.; Kant, J. Tetrahedron Lett. 1992, 33, 3563. (s) Farina, V.; Kant, J. Tetrahedron Lett. 1992, 33, 3559. (t) Broggini, G.; Bruché, L.; Zecchi, G. J. Chem. Soc., Perkin Trans. 1 1990, 533. (u) Nilsson, B. M.; Hacksell, U. J. Heterocycl. Chem. 1989, 26, 269. (v) Jones, B. C. N. M.; Silverton, J. V.; Simons, C.; Megati, S.; Nishimura, H.; Maeda, Y.; Mitsuya, H.; Zemlicka, J. J. Med. Chem. 1995, 38, 1397. (w) Rádl, S.; Kovárová, L. Collect. Czech. Chem. Commun. 1991, 56, 2413. (x) For an account on living polymerization of allenamides, see: Takagi, K.; Tomita, I.; Endo, T. Macromolecules 1998, 31, 6741.
18. For recent chemistry using allenamides, see: (a) Gaul, C.; Seebach, D. Helv. Chim. Acta 2002, 85, 963. (b) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 1499. (c) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2001, 42, 4869. (d) Kinderman, S. S.; van Maarseveen, J. H.; Schoemaker, H. E.; Hiemstra, H.; Rutjes, F. P. T. Org. Lett. 2001, 3, 2045. (e) van Boxtel, L. J.; Korbe, S.; Noltemeyer, M.; de Meijere, A. Eur. J. Org. Chem. 2001, 2283. (f) Grigg, R.; Köppen, I.; Rasparini, M.; Sridharan, V. Chem. Commun. 2001, 964. (g) Gardiner, M.; Grigg, R.; Sridharan, V.; Vicker, N. Tetrahedron Lett. 1998, 39, 435. (h) Grigg, R.; Sansano, J. M.; Santhakumar, V.; Sridharan, V.; Thangavelanthum, R.; Thornton-Pett, M.; Wilson, D. Tetrahedron 1997, 53, 11803. (i) Grigg, R.; Loganathan, V.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S.; Worakun, T. Tetrahedron 1996, 52, 11479. (j) Griggs, R.; Sansano, J. M. Tetrahedron 1996, 52, 13441. (k) Grigg, R.; Sridharan, V.; Xu, L.-H. J. Chem. Soc., Chem. Commun. 1995, 1903. (l) Kimura, M.; Horino, Y.; Wakamiya, Y.; Okajima, T.; Tamaru, Y. J. Am. Chem. Soc. 1997, 119, 10869. (m) Kimura, M.; Wakamiya, Y.; Horino, Y.; Tamaru, Y. Tetrahedron Lett. 1997, 38, 3963. (n) Horino, Y.; Kimura, M.; Wakamiya, Y.; Okajima, T.; Tamaru, Y. Angew. Chem. Int. Ed. 1999, 38, 121. (o) Noguchi, M.; Okada, H.; Wantanabe, M.; Okuda, K.; Nakamura, O. Tetrahedron 1996, 52, 6581. (p) Gericke, R.; Lues, I. Tetrahedron Lett. 1992, 33, 1871. (q) Tanaka, H.; Kameyama, Y.; Sumida, S.; Yamada, T.; Tokumaru, Y.; Shiroi, T.; Sasaoka, M.; Taniguchi, M.; Torri, S. Synlett 1991, 888. (r) Farina, V.; Kant, J. Tetrahedron Lett. 1992, 33, 3563. (s) Farina, V.; Kant, J. Tetrahedron Lett. 1992, 33, 3559. (t) Broggini, G.; Bruché, L.; Zecchi, G. J. Chem. Soc., Perkin Trans. 1 1990, 533. (u) Nilsson, B. M.; Hacksell, U. J. Heterocycl. Chem. 1989, 26, 269. (v) Jones, B. C. N. M.; Silverton, J. V.; Simons, C.; Megati, S.; Nishimura, H.; Maeda, Y.; Mitsuya, H.; Zemlicka, J. J. Med. Chem. 1995, 38, 1397. (w) Rádl, S.; Kovárová, L. Collect. Czech. Chem. Commun. 1991, 56, 2413. (x) For an account on living polymerization of allenamides, see: Takagi, K.; Tomita, I.; Endo, T. Macromolecules 1998, 31, 6741.
19. For recent chemistry using allenamides, see: (a) Gaul, C.; Seebach, D. Helv. Chim. Acta 2002, 85, 963. (b) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 1499. (c) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2001, 42, 4869. (d) Kinderman, S. S.; van Maarseveen, J. H.; Schoemaker, H. E.; Hiemstra, H.; Rutjes, F. P. T. Org. Lett. 2001, 3, 2045. (e) van Boxtel, L. J.; Korbe, S.; Noltemeyer, M.; de Meijere, A. Eur. J. Org. Chem. 2001, 2283. (f) Grigg, R.; Köppen, I.; Rasparini, M.; Sridharan, V. Chem. Commun. 2001, 964. (g) Gardiner, M.; Grigg, R.; Sridharan, V.; Vicker, N. Tetrahedron Lett. 1998, 39, 435. (h) Grigg, R.; Sansano, J. M.; Santhakumar, V.; Sridharan, V.; Thangavelanthum, R.; Thornton-Pett, M.; Wilson, D. Tetrahedron 1997, 53, 11803. (i) Grigg, R.; Loganathan, V.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S.; Worakun, T. Tetrahedron 1996, 52, 11479. (j) Griggs, R.; Sansano, J. M. Tetrahedron 1996, 52, 13441. (k) Grigg, R.; Sridharan, V.; Xu, L.-H. J. Chem. Soc., Chem. Commun. 1995, 1903. (l) Kimura, M.; Horino, Y.; Wakamiya, Y.; Okajima, T.; Tamaru, Y. J. Am. Chem. Soc. 1997, 119, 10869. (m) Kimura, M.; Wakamiya, Y.; Horino, Y.; Tamaru, Y. Tetrahedron Lett. 1997, 38, 3963. (n) Horino, Y.; Kimura, M.; Wakamiya, Y.; Okajima, T.; Tamaru, Y. Angew. Chem. Int. Ed. 1999, 38, 121. (o) Noguchi, M.; Okada, H.; Wantanabe, M.; Okuda, K.; Nakamura, O. Tetrahedron 1996, 52, 6581. (p) Gericke, R.; Lues, I. Tetrahedron Lett. 1992, 33, 1871. (q) Tanaka, H.; Kameyama, Y.; Sumida, S.; Yamada, T.; Tokumaru, Y.; Shiroi, T.; Sasaoka, M.; Taniguchi, M.; Torri, S. Synlett 1991, 888. (r) Farina, V.; Kant, J. Tetrahedron Lett. 1992, 33, 3563. (s) Farina, V.; Kant, J. Tetrahedron Lett. 1992, 33, 3559. (t) Broggini, G.; Bruché, L.; Zecchi, G. J. Chem. Soc., Perkin Trans. 1 1990, 533. (u) Nilsson, B. M.; Hacksell, U. J. Heterocycl. Chem. 1989, 26, 269. (v) Jones, B. C. N. M.; Silverton, J. V.; Simons, C.; Megati, S.; Nishimura, H.; Maeda, Y.; Mitsuya, H.; Zemlicka, J. J. Med. Chem. 1995, 38, 1397. (w) Rádl, S.; Kovárová, L. Collect. Czech. Chem. Commun. 1991, 56, 2413. (x) For an account on living polymerization of allenamides, see: Takagi, K.; Tomita, I.; Endo, T. Macromolecules 1998, 31, 6741.
20. For recent chemistry using allenamides, see: (a) Gaul, C.; Seebach, D. Helv. Chim. Acta 2002, 85, 963. (b) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 1499. (c) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2001, 42, 4869. (d) Kinderman, S. S.; van Maarseveen, J. H.; Schoemaker, H. E.; Hiemstra, H.; Rutjes, F. P. T. Org. Lett. 2001, 3, 2045. (e) van Boxtel, L. J.; Korbe, S.; Noltemeyer, M.; de Meijere, A. Eur. J. Org. Chem. 2001, 2283. (f) Grigg, R.; Köppen, I.; Rasparini, M.; Sridharan, V. Chem. Commun. 2001, 964. (g) Gardiner, M.; Grigg, R.; Sridharan, V.; Vicker, N. Tetrahedron Lett. 1998, 39, 435. (h) Grigg, R.; Sansano, J. M.; Santhakumar, V.; Sridharan, V.; Thangavelanthum, R.; Thornton-Pett, M.; Wilson, D. Tetrahedron 1997, 53, 11803. (i) Grigg, R.; Loganathan, V.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S.; Worakun, T. Tetrahedron 1996, 52, 11479. (j) Griggs, R.; Sansano, J. M. Tetrahedron 1996, 52, 13441. (k) Grigg, R.; Sridharan, V.; Xu, L.-H. J. Chem. Soc., Chem. Commun. 1995, 1903. (l) Kimura, M.; Horino, Y.; Wakamiya, Y.; Okajima, T.; Tamaru, Y. J. Am. Chem. Soc. 1997, 119, 10869. (m) Kimura, M.; Wakamiya, Y.; Horino, Y.; Tamaru, Y. Tetrahedron Lett. 1997, 38, 3963. (n) Horino, Y.; Kimura, M.; Wakamiya, Y.; Okajima, T.; Tamaru, Y. Angew. Chem. Int. Ed. 1999, 38, 121. (o) Noguchi, M.; Okada, H.; Wantanabe, M.; Okuda, K.; Nakamura, O. Tetrahedron 1996, 52, 6581. (p) Gericke, R.; Lues, I. Tetrahedron Lett. 1992, 33, 1871. (q) Tanaka, H.; Kameyama, Y.; Sumida, S.; Yamada, T.; Tokumaru, Y.; Shiroi, T.; Sasaoka, M.; Taniguchi, M.; Torri, S. Synlett 1991, 888. (r) Farina, V.; Kant, J. Tetrahedron Lett. 1992, 33, 3563. (s) Farina, V.; Kant, J. Tetrahedron Lett. 1992, 33, 3559. (t) Broggini, G.; Bruché, L.; Zecchi, G. J. Chem. Soc., Perkin Trans. 1 1990, 533. (u) Nilsson, B. M.; Hacksell, U. J. Heterocycl. Chem. 1989, 26, 269. (v) Jones, B. C. N. M.; Silverton, J. V.; Simons, C.; Megati, S.; Nishimura, H.; Maeda, Y.; Mitsuya, H.; Zemlicka, J. J. Med. Chem. 1995, 38, 1397. (w) Rádl, S.; Kovárová, L. Collect. Czech. Chem. Commun. 1991, 56, 2413. (x) For an account on living polymerization of allenamides, see: Takagi, K.; Tomita, I.; Endo, T. Macromolecules 1998, 31, 6741.
21. For recent chemistry using allenamides, see: (a) Gaul, C.; Seebach, D. Helv. Chim. Acta 2002, 85, 963. (b) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 1499. (c) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2001, 42, 4869. (d) Kinderman, S. S.; van Maarseveen, J. H.; Schoemaker, H. E.; Hiemstra, H.; Rutjes, F. P. T. Org. Lett. 2001, 3, 2045. (e) van Boxtel, L. J.; Korbe, S.; Noltemeyer, M.; de Meijere, A. Eur. J. Org. Chem. 2001, 2283. (f) Grigg, R.; Köppen, I.; Rasparini, M.; Sridharan, V. Chem. Commun. 2001, 964. (g) Gardiner, M.; Grigg, R.; Sridharan, V.; Vicker, N. Tetrahedron Lett. 1998, 39, 435. (h) Grigg, R.; Sansano, J. M.; Santhakumar, V.; Sridharan, V.; Thangavelanthum, R.; Thornton-Pett, M.; Wilson, D. Tetrahedron 1997, 53, 11803. (i) Grigg, R.; Loganathan, V.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S.; Worakun, T. Tetrahedron 1996, 52, 11479. (j) Griggs, R.; Sansano, J. M. Tetrahedron 1996, 52, 13441. (k) Grigg, R.; Sridharan, V.; Xu, L.-H. J. Chem. Soc., Chem. Commun. 1995, 1903. (l) Kimura, M.; Horino, Y.; Wakamiya, Y.; Okajima, T.; Tamaru, Y. J. Am. Chem. Soc. 1997, 119, 10869. (m) Kimura, M.; Wakamiya, Y.; Horino, Y.; Tamaru, Y. Tetrahedron Lett. 1997, 38, 3963. (n) Horino, Y.; Kimura, M.; Wakamiya, Y.; Okajima, T.; Tamaru, Y. Angew. Chem. Int. Ed. 1999, 38, 121. (o) Noguchi, M.; Okada, H.; Wantanabe, M.; Okuda, K.; Nakamura, O. Tetrahedron 1996, 52, 6581. (p) Gericke, R.; Lues, I. Tetrahedron Lett. 1992, 33, 1871. (q) Tanaka, H.; Kameyama, Y.; Sumida, S.; Yamada, T.; Tokumaru, Y.; Shiroi, T.; Sasaoka, M.; Taniguchi, M.; Torri, S. Synlett 1991, 888. (r) Farina, V.; Kant, J. Tetrahedron Lett. 1992, 33, 3563. (s) Farina, V.; Kant, J. Tetrahedron Lett. 1992, 33, 3559. (t) Broggini, G.; Bruché, L.; Zecchi, G. J. Chem. Soc., Perkin Trans. 1 1990, 533. (u) Nilsson, B. M.; Hacksell, U. J. Heterocycl. Chem. 1989, 26, 269. (v) Jones, B. C. N. M.; Silverton, J. V.; Simons, C.; Megati, S.; Nishimura, H.; Maeda, Y.; Mitsuya, H.; Zemlicka, J. J. Med. Chem. 1995, 38, 1397. (w) Rádl, S.; Kovárová, L. Collect. Czech. Chem. Commun. 1991, 56, 2413. (x) For an account on living polymerization of allenamides, see: Takagi, K.; Tomita, I.; Endo, T. Macromolecules 1998, 31, 6741.
22. For recent chemistry using allenamides, see: (a) Gaul, C.; Seebach, D. Helv. Chim. Acta 2002, 85, 963. (b) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 1499. (c) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2001, 42, 4869. (d) Kinderman, S. S.; van Maarseveen, J. H.; Schoemaker, H. E.; Hiemstra, H.; Rutjes, F. P. T. Org. Lett. 2001, 3, 2045. (e) van Boxtel, L. J.; Korbe, S.; Noltemeyer, M.; de Meijere, A. Eur. J. Org. Chem. 2001, 2283. (f) Grigg, R.; Köppen, I.; Rasparini, M.; Sridharan, V. Chem. Commun. 2001, 964. (g) Gardiner, M.; Grigg, R.; Sridharan, V.; Vicker, N. Tetrahedron Lett. 1998, 39, 435. (h) Grigg, R.; Sansano, J. M.; Santhakumar, V.; Sridharan, V.; Thangavelanthum, R.; Thornton-Pett, M.; Wilson, D. Tetrahedron 1997, 53, 11803. (i) Grigg, R.; Loganathan, V.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S.; Worakun, T. Tetrahedron 1996, 52, 11479. (j) Griggs, R.; Sansano, J. M. Tetrahedron 1996, 52, 13441. (k) Grigg, R.; Sridharan, V.; Xu, L.-H. J. Chem. Soc., Chem. Commun. 1995, 1903. (l) Kimura, M.; Horino, Y.; Wakamiya, Y.; Okajima, T.; Tamaru, Y. J. Am. Chem. Soc. 1997, 119, 10869. (m) Kimura, M.; Wakamiya, Y.; Horino, Y.; Tamaru, Y. Tetrahedron Lett. 1997, 38, 3963. (n) Horino, Y.; Kimura, M.; Wakamiya, Y.; Okajima, T.; Tamaru, Y. Angew. Chem. Int. Ed. 1999, 38, 121. (o) Noguchi, M.; Okada, H.; Wantanabe, M.; Okuda, K.; Nakamura, O. Tetrahedron 1996, 52, 6581. (p) Gericke, R.; Lues, I. Tetrahedron Lett. 1992, 33, 1871. (q) Tanaka, H.; Kameyama, Y.; Sumida, S.; Yamada, T.; Tokumaru, Y.; Shiroi, T.; Sasaoka, M.; Taniguchi, M.; Torri, S. Synlett 1991, 888. (r) Farina, V.; Kant, J. Tetrahedron Lett. 1992, 33, 3563. (s) Farina, V.; Kant, J. Tetrahedron Lett. 1992, 33, 3559. (t) Broggini, G.; Bruché, L.; Zecchi, G. J. Chem. Soc., Perkin Trans. 1 1990, 533. (u) Nilsson, B. M.; Hacksell, U. J. Heterocycl. Chem. 1989, 26, 269. (v) Jones, B. C. N. M.; Silverton, J. V.; Simons, C.; Megati, S.; Nishimura, H.; Maeda, Y.; Mitsuya, H.; Zemlicka, J. J. Med. Chem. 1995, 38, 1397. (w) Rádl, S.; Kovárová, L. Collect. Czech. Chem. Commun. 1991, 56, 2413. (x) For an account on living polymerization of allenamides, see: Takagi, K.; Tomita, I.; Endo, T. Macromolecules 1998, 31, 6741.
23. For recent chemistry using allenamides, see: (a) Gaul, C.; Seebach, D. Helv. Chim. Acta 2002, 85, 963. (b) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 1499. (c) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2001, 42, 4869. (d) Kinderman, S. S.; van Maarseveen, J. H.; Schoemaker, H. E.; Hiemstra, H.; Rutjes, F. P. T. Org. Lett. 2001, 3, 2045. (e) van Boxtel, L. J.; Korbe, S.; Noltemeyer, M.; de Meijere, A. Eur. J. Org. Chem. 2001, 2283. (f) Grigg, R.; Köppen, I.; Rasparini, M.; Sridharan, V. Chem. Commun. 2001, 964. (g) Gardiner, M.; Grigg, R.; Sridharan, V.; Vicker, N. Tetrahedron Lett. 1998, 39, 435. (h) Grigg, R.; Sansano, J. M.; Santhakumar, V.; Sridharan, V.; Thangavelanthum, R.; Thornton-Pett, M.; Wilson, D. Tetrahedron 1997, 53, 11803. (i) Grigg, R.; Loganathan, V.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S.; Worakun, T. Tetrahedron 1996, 52, 11479. (j) Griggs, R.; Sansano, J. M. Tetrahedron 1996, 52, 13441. (k) Grigg, R.; Sridharan, V.; Xu, L.-H. J. Chem. Soc., Chem. Commun. 1995, 1903. (l) Kimura, M.; Horino, Y.; Wakamiya, Y.; Okajima, T.; Tamaru, Y. J. Am. Chem. Soc. 1997, 119, 10869. (m) Kimura, M.; Wakamiya, Y.; Horino, Y.; Tamaru, Y. Tetrahedron Lett. 1997, 38, 3963. (n) Horino, Y.; Kimura, M.; Wakamiya, Y.; Okajima, T.; Tamaru, Y. Angew. Chem. Int. Ed. 1999, 38, 121. (o) Noguchi, M.; Okada, H.; Wantanabe, M.; Okuda, K.; Nakamura, O. Tetrahedron 1996, 52, 6581. (p) Gericke, R.; Lues, I. Tetrahedron Lett. 1992, 33, 1871. (q) Tanaka, H.; Kameyama, Y.; Sumida, S.; Yamada, T.; Tokumaru, Y.; Shiroi, T.; Sasaoka, M.; Taniguchi, M.; Torri, S. Synlett 1991, 888. (r) Farina, V.; Kant, J. Tetrahedron Lett. 1992, 33, 3563. (s) Farina, V.; Kant, J. Tetrahedron Lett. 1992, 33, 3559. (t) Broggini, G.; Bruché, L.; Zecchi, G. J. Chem. Soc., Perkin Trans. 1 1990, 533. (u) Nilsson, B. M.; Hacksell, U. J. Heterocycl. Chem. 1989, 26, 269. (v) Jones, B. C. N. M.; Silverton, J. V.; Simons, C.; Megati, S.; Nishimura, H.; Maeda, Y.; Mitsuya, H.; Zemlicka, J. J. Med. Chem. 1995, 38, 1397. (w) Rádl, S.; Kovárová, L. Collect. Czech. Chem. Commun. 1991, 56, 2413. (x) For an account on living polymerization of allenamides, see: Takagi, K.; Tomita, I.; Endo, T. Macromolecules 1998, 31, 6741.
24. For recent chemistry using allenamides, see: (a) Gaul, C.; Seebach, D. Helv. Chim. Acta 2002, 85, 963. (b) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 1499. (c) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2001, 42, 4869. (d) Kinderman, S. S.; van Maarseveen, J. H.; Schoemaker, H. E.; Hiemstra, H.; Rutjes, F. P. T. Org. Lett. 2001, 3, 2045. (e) van Boxtel, L. J.; Korbe, S.; Noltemeyer, M.; de Meijere, A. Eur. J. Org. Chem. 2001, 2283. (f) Grigg, R.; Köppen, I.; Rasparini, M.; Sridharan, V. Chem. Commun. 2001, 964. (g) Gardiner, M.; Grigg, R.; Sridharan, V.; Vicker, N. Tetrahedron Lett. 1998, 39, 435. (h) Grigg, R.; Sansano, J. M.; Santhakumar, V.; Sridharan, V.; Thangavelanthum, R.; Thornton-Pett, M.; Wilson, D. Tetrahedron 1997, 53, 11803. (i) Grigg, R.; Loganathan, V.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S.; Worakun, T. Tetrahedron 1996, 52, 11479. (j) Griggs, R.; Sansano, J. M. Tetrahedron 1996, 52, 13441. (k) Grigg, R.; Sridharan, V.; Xu, L.-H. J. Chem. Soc., Chem. Commun. 1995, 1903. (l) Kimura, M.; Horino, Y.; Wakamiya, Y.; Okajima, T.; Tamaru, Y. J. Am. Chem. Soc. 1997, 119, 10869. (m) Kimura, M.; Wakamiya, Y.; Horino, Y.; Tamaru, Y. Tetrahedron Lett. 1997, 38, 3963. (n) Horino, Y.; Kimura, M.; Wakamiya, Y.; Okajima, T.; Tamaru, Y. Angew. Chem. Int. Ed. 1999, 38, 121. (o) Noguchi, M.; Okada, H.; Wantanabe, M.; Okuda, K.; Nakamura, O. Tetrahedron 1996, 52, 6581. (p) Gericke, R.; Lues, I. Tetrahedron Lett. 1992, 33, 1871. (q) Tanaka, H.; Kameyama, Y.; Sumida, S.; Yamada, T.; Tokumaru, Y.; Shiroi, T.; Sasaoka, M.; Taniguchi, M.; Torri, S. Synlett 1991, 888. (r) Farina, V.; Kant, J. Tetrahedron Lett. 1992, 33, 3563. (s) Farina, V.; Kant, J. Tetrahedron Lett. 1992, 33, 3559. (t) Broggini, G.; Bruché, L.; Zecchi, G. J. Chem. Soc., Perkin Trans. 1 1990, 533. (u) Nilsson, B. M.; Hacksell, U. J. Heterocycl. Chem. 1989, 26, 269. (v) Jones, B. C. N. M.; Silverton, J. V.; Simons, C.; Megati, S.; Nishimura, H.; Maeda, Y.; Mitsuya, H.; Zemlicka, J. J. Med. Chem. 1995, 38, 1397. (w) Rádl, S.; Kovárová, L. Collect. Czech. Chem. Commun. 1991, 56, 2413. (x) For an account on living polymerization of allenamides, see: Takagi, K.; Tomita, I.; Endo, T. Macromolecules 1998, 31, 6741.
25. For recent chemistry using allenamides, see: (a) Gaul, C.; Seebach, D. Helv. Chim. Acta 2002, 85, 963. (b) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 1499. (c) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2001, 42, 4869. (d) Kinderman, S. S.; van Maarseveen, J. H.; Schoemaker, H. E.; Hiemstra, H.; Rutjes, F. P. T. Org. Lett. 2001, 3, 2045. (e) van Boxtel, L. J.; Korbe, S.; Noltemeyer, M.; de Meijere, A. Eur. J. Org. Chem. 2001, 2283. (f) Grigg, R.; Köppen, I.; Rasparini, M.; Sridharan, V. Chem. Commun. 2001, 964. (g) Gardiner, M.; Grigg, R.; Sridharan, V.; Vicker, N. Tetrahedron Lett. 1998, 39, 435. (h) Grigg, R.; Sansano, J. M.; Santhakumar, V.; Sridharan, V.; Thangavelanthum, R.; Thornton-Pett, M.; Wilson, D. Tetrahedron 1997, 53, 11803. (i) Grigg, R.; Loganathan, V.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S.; Worakun, T. Tetrahedron 1996, 52, 11479. (j) Griggs, R.; Sansano, J. M. Tetrahedron 1996, 52, 13441. (k) Grigg, R.; Sridharan, V.; Xu, L.-H. J. Chem. Soc., Chem. Commun. 1995, 1903. (l) Kimura, M.; Horino, Y.; Wakamiya, Y.; Okajima, T.; Tamaru, Y. J. Am. Chem. Soc. 1997, 119, 10869. (m) Kimura, M.; Wakamiya, Y.; Horino, Y.; Tamaru, Y. Tetrahedron Lett. 1997, 38, 3963. (n) Horino, Y.; Kimura, M.; Wakamiya, Y.; Okajima, T.; Tamaru, Y. Angew. Chem. Int. Ed. 1999, 38, 121. (o) Noguchi, M.; Okada, H.; Wantanabe, M.; Okuda, K.; Nakamura, O. Tetrahedron 1996, 52, 6581. (p) Gericke, R.; Lues, I. Tetrahedron Lett. 1992, 33, 1871. (q) Tanaka, H.; Kameyama, Y.; Sumida, S.; Yamada, T.; Tokumaru, Y.; Shiroi, T.; Sasaoka, M.; Taniguchi, M.; Torri, S. Synlett 1991, 888. (r) Farina, V.; Kant, J. Tetrahedron Lett. 1992, 33, 3563. (s) Farina, V.; Kant, J. Tetrahedron Lett. 1992, 33, 3559. (t) Broggini, G.; Bruché, L.; Zecchi, G. J. Chem. Soc., Perkin Trans. 1 1990, 533. (u) Nilsson, B. M.; Hacksell, U. J. Heterocycl. Chem. 1989, 26, 269. (v) Jones, B. C. N. M.; Silverton, J. V.; Simons, C.; Megati, S.; Nishimura, H.; Maeda, Y.; Mitsuya, H.; Zemlicka, J. J. Med. Chem. 1995, 38, 1397. (w) Rádl, S.; Kovárová, L. Collect. Czech. Chem. Commun. 1991, 56, 2413. (x) For an account on living polymerization of allenamides, see: Takagi, K.; Tomita, I.; Endo, T. Macromolecules 1998, 31, 6741.
26. For recent chemistry using allenamides, see: (a) Gaul, C.; Seebach, D. Helv. Chim. Acta 2002, 85, 963. (b) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 1499. (c) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2001, 42, 4869. (d) Kinderman, S. S.; van Maarseveen, J. H.; Schoemaker, H. E.; Hiemstra, H.; Rutjes, F. P. T. Org. Lett. 2001, 3, 2045. (e) van Boxtel, L. J.; Korbe, S.; Noltemeyer, M.; de Meijere, A. Eur. J. Org. Chem. 2001, 2283. (f) Grigg, R.; Köppen, I.; Rasparini, M.; Sridharan, V. Chem. Commun. 2001, 964. (g) Gardiner, M.; Grigg, R.; Sridharan, V.; Vicker, N. Tetrahedron Lett. 1998, 39, 435. (h) Grigg, R.; Sansano, J. M.; Santhakumar, V.; Sridharan, V.; Thangavelanthum, R.; Thornton-Pett, M.; Wilson, D. Tetrahedron 1997, 53, 11803. (i) Grigg, R.; Loganathan, V.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S.; Worakun, T. Tetrahedron 1996, 52, 11479. (j) Griggs, R.; Sansano, J. M. Tetrahedron 1996, 52, 13441. (k) Grigg, R.; Sridharan, V.; Xu, L.-H. J. Chem. Soc., Chem. Commun. 1995, 1903. (l) Kimura, M.; Horino, Y.; Wakamiya, Y.; Okajima, T.; Tamaru, Y. J. Am. Chem. Soc. 1997, 119, 10869. (m) Kimura, M.; Wakamiya, Y.; Horino, Y.; Tamaru, Y. Tetrahedron Lett. 1997, 38, 3963. (n) Horino, Y.; Kimura, M.; Wakamiya, Y.; Okajima, T.; Tamaru, Y. Angew. Chem. Int. Ed. 1999, 38, 121. (o) Noguchi, M.; Okada, H.; Wantanabe, M.; Okuda, K.; Nakamura, O. Tetrahedron 1996, 52, 6581. (p) Gericke, R.; Lues, I. Tetrahedron Lett. 1992, 33, 1871. (q) Tanaka, H.; Kameyama, Y.; Sumida, S.; Yamada, T.; Tokumaru, Y.; Shiroi, T.; Sasaoka, M.; Taniguchi, M.; Torri, S. Synlett 1991, 888. (r) Farina, V.; Kant, J. Tetrahedron Lett. 1992, 33, 3563. (s) Farina, V.; Kant, J. Tetrahedron Lett. 1992, 33, 3559. (t) Broggini, G.; Bruché, L.; Zecchi, G. J. Chem. Soc., Perkin Trans. 1 1990, 533. (u) Nilsson, B. M.; Hacksell, U. J. Heterocycl. Chem. 1989, 26, 269. (v) Jones, B. C. N. M.; Silverton, J. V.; Simons, C.; Megati, S.; Nishimura, H.; Maeda, Y.; Mitsuya, H.; Zemlicka, J. J. Med. Chem. 1995, 38, 1397. (w) Rádl, S.; Kovárová, L. Collect. Czech. Chem. Commun. 1991, 56, 2413. (x) For an account on living polymerization of allenamides, see: Takagi, K.; Tomita, I.; Endo, T. Macromolecules 1998, 31, 6741.
27. For recent chemistry using allenamides, see: (a) Gaul, C.; Seebach, D. Helv. Chim. Acta 2002, 85, 963. (b) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 1499. (c) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2001, 42, 4869. (d) Kinderman, S. S.; van Maarseveen, J. H.; Schoemaker, H. E.; Hiemstra, H.; Rutjes, F. P. T. Org. Lett. 2001, 3, 2045. (e) van Boxtel, L. J.; Korbe, S.; Noltemeyer, M.; de Meijere, A. Eur. J. Org. Chem. 2001, 2283. (f) Grigg, R.; Köppen, I.; Rasparini, M.; Sridharan, V. Chem. Commun. 2001, 964. (g) Gardiner, M.; Grigg, R.; Sridharan, V.; Vicker, N. Tetrahedron Lett. 1998, 39, 435. (h) Grigg, R.; Sansano, J. M.; Santhakumar, V.; Sridharan, V.; Thangavelanthum, R.; Thornton-Pett, M.; Wilson, D. Tetrahedron 1997, 53, 11803. (i) Grigg, R.; Loganathan, V.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S.; Worakun, T. Tetrahedron 1996, 52, 11479. (j) Griggs, R.; Sansano, J. M. Tetrahedron 1996, 52, 13441. (k) Grigg, R.; Sridharan, V.; Xu, L.-H. J. Chem. Soc., Chem. Commun. 1995, 1903. (l) Kimura, M.; Horino, Y.; Wakamiya, Y.; Okajima, T.; Tamaru, Y. J. Am. Chem. Soc. 1997, 119, 10869. (m) Kimura, M.; Wakamiya, Y.; Horino, Y.; Tamaru, Y. Tetrahedron Lett. 1997, 38, 3963. (n) Horino, Y.; Kimura, M.; Wakamiya, Y.; Okajima, T.; Tamaru, Y. Angew. Chem. Int. Ed. 1999, 38, 121. (o) Noguchi, M.; Okada, H.; Wantanabe, M.; Okuda, K.; Nakamura, O. Tetrahedron 1996, 52, 6581. (p) Gericke, R.; Lues, I. Tetrahedron Lett. 1992, 33, 1871. (q) Tanaka, H.; Kameyama, Y.; Sumida, S.; Yamada, T.; Tokumaru, Y.; Shiroi, T.; Sasaoka, M.; Taniguchi, M.; Torri, S. Synlett 1991, 888. (r) Farina, V.; Kant, J. Tetrahedron Lett. 1992, 33, 3563. (s) Farina, V.; Kant, J. Tetrahedron Lett. 1992, 33, 3559. (t) Broggini, G.; Bruché, L.; Zecchi, G. J. Chem. Soc., Perkin Trans. 1 1990, 533. (u) Nilsson, B. M.; Hacksell, U. J. Heterocycl. Chem. 1989, 26, 269. (v) Jones, B. C. N. M.; Silverton, J. V.; Simons, C.; Megati, S.; Nishimura, H.; Maeda, Y.; Mitsuya, H.; Zemlicka, J. J. Med. Chem. 1995, 38, 1397. (w) Rádl, S.; Kovárová, L. Collect. Czech. Chem. Commun. 1991, 56, 2413. (x) For an account on living polymerization of allenamides, see: Takagi, K.; Tomita, I.; Endo, T. Macromolecules 1998, 31, 6741.
28. For recent chemistry using allenamides, see: (a) Gaul, C.; Seebach, D. Helv. Chim. Acta 2002, 85, 963. (b) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 1499. (c) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2001, 42, 4869. (d) Kinderman, S. S.; van Maarseveen, J. H.; Schoemaker, H. E.; Hiemstra, H.; Rutjes, F. P. T. Org. Lett. 2001, 3, 2045. (e) van Boxtel, L. J.; Korbe, S.; Noltemeyer, M.; de Meijere, A. Eur. J. Org. Chem. 2001, 2283. (f) Grigg, R.; Köppen, I.; Rasparini, M.; Sridharan, V. Chem. Commun. 2001, 964. (g) Gardiner, M.; Grigg, R.; Sridharan, V.; Vicker, N. Tetrahedron Lett. 1998, 39, 435. (h) Grigg, R.; Sansano, J. M.; Santhakumar, V.; Sridharan, V.; Thangavelanthum, R.; Thornton-Pett, M.; Wilson, D. Tetrahedron 1997, 53, 11803. (i) Grigg, R.; Loganathan, V.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S.; Worakun, T. Tetrahedron 1996, 52, 11479. (j) Griggs, R.; Sansano, J. M. Tetrahedron 1996, 52, 13441. (k) Grigg, R.; Sridharan, V.; Xu, L.-H. J. Chem. Soc., Chem. Commun. 1995, 1903. (l) Kimura, M.; Horino, Y.; Wakamiya, Y.; Okajima, T.; Tamaru, Y. J. Am. Chem. Soc. 1997, 119, 10869. (m) Kimura, M.; Wakamiya, Y.; Horino, Y.; Tamaru, Y. Tetrahedron Lett. 1997, 38, 3963. (n) Horino, Y.; Kimura, M.; Wakamiya, Y.; Okajima, T.; Tamaru, Y. Angew. Chem. Int. Ed. 1999, 38, 121. (o) Noguchi, M.; Okada, H.; Wantanabe, M.; Okuda, K.; Nakamura, O. Tetrahedron 1996, 52, 6581. (p) Gericke, R.; Lues, I. Tetrahedron Lett. 1992, 33, 1871. (q) Tanaka, H.; Kameyama, Y.; Sumida, S.; Yamada, T.; Tokumaru, Y.; Shiroi, T.; Sasaoka, M.; Taniguchi, M.; Torri, S. Synlett 1991, 888. (r) Farina, V.; Kant, J. Tetrahedron Lett. 1992, 33, 3563. (s) Farina, V.; Kant, J. Tetrahedron Lett. 1992, 33, 3559. (t) Broggini, G.; Bruché, L.; Zecchi, G. J. Chem. Soc., Perkin Trans. 1 1990, 533. (u) Nilsson, B. M.; Hacksell, U. J. Heterocycl. Chem. 1989, 26, 269. (v) Jones, B. C. N. M.; Silverton, J. V.; Simons, C.; Megati, S.; Nishimura, H.; Maeda, Y.; Mitsuya, H.; Zemlicka, J. J. Med. Chem. 1995, 38, 1397. (w) Rádl, S.; Kovárová, L. Collect. Czech. Chem. Commun. 1991, 56, 2413. (x) For an account on living polymerization of allenamides, see: Takagi, K.; Tomita, I.; Endo, T. Macromolecules 1998, 31, 6741.
29. For recent chemistry using allenamides, see: (a) Gaul, C.; Seebach, D. Helv. Chim. Acta 2002, 85, 963. (b) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 1499. (c) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2001, 42, 4869. (d) Kinderman, S. S.; van Maarseveen, J. H.; Schoemaker, H. E.; Hiemstra, H.; Rutjes, F. P. T. Org. Lett. 2001, 3, 2045. (e) van Boxtel, L. J.; Korbe, S.; Noltemeyer, M.; de Meijere, A. Eur. J. Org. Chem. 2001, 2283. (f) Grigg, R.; Köppen, I.; Rasparini, M.; Sridharan, V. Chem. Commun. 2001, 964. (g) Gardiner, M.; Grigg, R.; Sridharan, V.; Vicker, N. Tetrahedron Lett. 1998, 39, 435. (h) Grigg, R.; Sansano, J. M.; Santhakumar, V.; Sridharan, V.; Thangavelanthum, R.; Thornton-Pett, M.; Wilson, D. Tetrahedron 1997, 53, 11803. (i) Grigg, R.; Loganathan, V.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S.; Worakun, T. Tetrahedron 1996, 52, 11479. (j) Griggs, R.; Sansano, J. M. Tetrahedron 1996, 52, 13441. (k) Grigg, R.; Sridharan, V.; Xu, L.-H. J. Chem. Soc., Chem. Commun. 1995, 1903. (l) Kimura, M.; Horino, Y.; Wakamiya, Y.; Okajima, T.; Tamaru, Y. J. Am. Chem. Soc. 1997, 119, 10869. (m) Kimura, M.; Wakamiya, Y.; Horino, Y.; Tamaru, Y. Tetrahedron Lett. 1997, 38, 3963. (n) Horino, Y.; Kimura, M.; Wakamiya, Y.; Okajima, T.; Tamaru, Y. Angew. Chem. Int. Ed. 1999, 38, 121. (o) Noguchi, M.; Okada, H.; Wantanabe, M.; Okuda, K.; Nakamura, O. Tetrahedron 1996, 52, 6581. (p) Gericke, R.; Lues, I. Tetrahedron Lett. 1992, 33, 1871. (q) Tanaka, H.; Kameyama, Y.; Sumida, S.; Yamada, T.; Tokumaru, Y.; Shiroi, T.; Sasaoka, M.; Taniguchi, M.; Torri, S. Synlett 1991, 888. (r) Farina, V.; Kant, J. Tetrahedron Lett. 1992, 33, 3563. (s) Farina, V.; Kant, J. Tetrahedron Lett. 1992, 33, 3559. (t) Broggini, G.; Bruché, L.; Zecchi, G. J. Chem. Soc., Perkin Trans. 1 1990, 533. (u) Nilsson, B. M.; Hacksell, U. J. Heterocycl. Chem. 1989, 26, 269. (v) Jones, B. C. N. M.; Silverton, J. V.; Simons, C.; Megati, S.; Nishimura, H.; Maeda, Y.; Mitsuya, H.; Zemlicka, J. J. Med. Chem. 1995, 38, 1397. (w) Rádl, S.; Kovárová, L. Collect. Czech. Chem. Commun. 1991, 56, 2413. (x) For an account on living polymerization of allenamides, see: Takagi, K.; Tomita, I.; Endo, T. Macromolecules 1998, 31, 6741.
30. For recent chemistry using allenamides, see: (a) Gaul, C.; Seebach, D. Helv. Chim. Acta 2002, 85, 963. (b) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 1499. (c) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2001, 42, 4869. (d) Kinderman, S. S.; van Maarseveen, J. H.; Schoemaker, H. E.; Hiemstra, H.; Rutjes, F. P. T. Org. Lett. 2001, 3, 2045. (e) van Boxtel, L. J.; Korbe, S.; Noltemeyer, M.; de Meijere, A. Eur. J. Org. Chem. 2001, 2283. (f) Grigg, R.; Köppen, I.; Rasparini, M.; Sridharan, V. Chem. Commun. 2001, 964. (g) Gardiner, M.; Grigg, R.; Sridharan, V.; Vicker, N. Tetrahedron Lett. 1998, 39, 435. (h) Grigg, R.; Sansano, J. M.; Santhakumar, V.; Sridharan, V.; Thangavelanthum, R.; Thornton-Pett, M.; Wilson, D. Tetrahedron 1997, 53, 11803. (i) Grigg, R.; Loganathan, V.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S.; Worakun, T. Tetrahedron 1996, 52, 11479. (j) Griggs, R.; Sansano, J. M. Tetrahedron 1996, 52, 13441. (k) Grigg, R.; Sridharan, V.; Xu, L.-H. J. Chem. Soc., Chem. Commun. 1995, 1903. (l) Kimura, M.; Horino, Y.; Wakamiya, Y.; Okajima, T.; Tamaru, Y. J. Am. Chem. Soc. 1997, 119, 10869. (m) Kimura, M.; Wakamiya, Y.; Horino, Y.; Tamaru, Y. Tetrahedron Lett. 1997, 38, 3963. (n) Horino, Y.; Kimura, M.; Wakamiya, Y.; Okajima, T.; Tamaru, Y. Angew. Chem. Int. Ed. 1999, 38, 121. (o) Noguchi, M.; Okada, H.; Wantanabe, M.; Okuda, K.; Nakamura, O. Tetrahedron 1996, 52, 6581. (p) Gericke, R.; Lues, I. Tetrahedron Lett. 1992, 33, 1871. (q) Tanaka, H.; Kameyama, Y.; Sumida, S.; Yamada, T.; Tokumaru, Y.; Shiroi, T.; Sasaoka, M.; Taniguchi, M.; Torri, S. Synlett 1991, 888. (r) Farina, V.; Kant, J. Tetrahedron Lett. 1992, 33, 3563. (s) Farina, V.; Kant, J. Tetrahedron Lett. 1992, 33, 3559. (t) Broggini, G.; Bruché, L.; Zecchi, G. J. Chem. Soc., Perkin Trans. 1 1990, 533. (u) Nilsson, B. M.; Hacksell, U. J. Heterocycl. Chem. 1989, 26, 269. (v) Jones, B. C. N. M.; Silverton, J. V.; Simons, C.; Megati, S.; Nishimura, H.; Maeda, Y.; Mitsuya, H.; Zemlicka, J. J. Med. Chem. 1995, 38, 1397. (w) Rádl, S.; Kovárová, L. Collect. Czech. Chem. Commun. 1991, 56, 2413. (x) For an account on living polymerization of allenamides, see: Takagi, K.; Tomita, I.; Endo, T. Macromolecules 1998, 31, 6741.
31. For recent chemistry using allenamides, see: (a) Gaul, C.; Seebach, D. Helv. Chim. Acta 2002, 85, 963. (b) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 1499. (c) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2001, 42, 4869. (d) Kinderman, S. S.; van Maarseveen, J. H.; Schoemaker, H. E.; Hiemstra, H.; Rutjes, F. P. T. Org. Lett. 2001, 3, 2045. (e) van Boxtel, L. J.; Korbe, S.; Noltemeyer, M.; de Meijere, A. Eur. J. Org. Chem. 2001, 2283. (f) Grigg, R.; Köppen, I.; Rasparini, M.; Sridharan, V. Chem. Commun. 2001, 964. (g) Gardiner, M.; Grigg, R.; Sridharan, V.; Vicker, N. Tetrahedron Lett. 1998, 39, 435. (h) Grigg, R.; Sansano, J. M.; Santhakumar, V.; Sridharan, V.; Thangavelanthum, R.; Thornton-Pett, M.; Wilson, D. Tetrahedron 1997, 53, 11803. (i) Grigg, R.; Loganathan, V.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S.; Worakun, T. Tetrahedron 1996, 52, 11479. (j) Griggs, R.; Sansano, J. M. Tetrahedron 1996, 52, 13441. (k) Grigg, R.; Sridharan, V.; Xu, L.-H. J. Chem. Soc., Chem. Commun. 1995, 1903. (l) Kimura, M.; Horino, Y.; Wakamiya, Y.; Okajima, T.; Tamaru, Y. J. Am. Chem. Soc. 1997, 119, 10869. (m) Kimura, M.; Wakamiya, Y.; Horino, Y.; Tamaru, Y. Tetrahedron Lett. 1997, 38, 3963. (n) Horino, Y.; Kimura, M.; Wakamiya, Y.; Okajima, T.; Tamaru, Y. Angew. Chem. Int. Ed. 1999, 38, 121. (o) Noguchi, M.; Okada, H.; Wantanabe, M.; Okuda, K.; Nakamura, O. Tetrahedron 1996, 52, 6581. (p) Gericke, R.; Lues, I. Tetrahedron Lett. 1992, 33, 1871. (q) Tanaka, H.; Kameyama, Y.; Sumida, S.; Yamada, T.; Tokumaru, Y.; Shiroi, T.; Sasaoka, M.; Taniguchi, M.; Torri, S. Synlett 1991, 888. (r) Farina, V.; Kant, J. Tetrahedron Lett. 1992, 33, 3563. (s) Farina, V.; Kant, J. Tetrahedron Lett. 1992, 33, 3559. (t) Broggini, G.; Bruché, L.; Zecchi, G. J. Chem. Soc., Perkin Trans. 1 1990, 533. (u) Nilsson, B. M.; Hacksell, U. J. Heterocycl. Chem. 1989, 26, 269. (v) Jones, B. C. N. M.; Silverton, J. V.; Simons, C.; Megati, S.; Nishimura, H.; Maeda, Y.; Mitsuya, H.; Zemlicka, J. J. Med. Chem. 1995, 38, 1397. (w) Rádl, S.; Kovárová, L. Collect. Czech. Chem. Commun. 1991, 56, 2413. (x) For an account on living polymerization of allenamides, see: Takagi, K.; Tomita, I.; Endo, T. Macromolecules 1998, 31, 6741.
32. For recent chemistry using allenamides, see: (a) Gaul, C.; Seebach, D. Helv. Chim. Acta 2002, 85, 963. (b) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 1499. (c) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2001, 42, 4869. (d) Kinderman, S. S.; van Maarseveen, J. H.; Schoemaker, H. E.; Hiemstra, H.; Rutjes, F. P. T. Org. Lett. 2001, 3, 2045. (e) van Boxtel, L. J.; Korbe, S.; Noltemeyer, M.; de Meijere, A. Eur. J. Org. Chem. 2001, 2283. (f) Grigg, R.; Köppen, I.; Rasparini, M.; Sridharan, V. Chem. Commun. 2001, 964. (g) Gardiner, M.; Grigg, R.; Sridharan, V.; Vicker, N. Tetrahedron Lett. 1998, 39, 435. (h) Grigg, R.; Sansano, J. M.; Santhakumar, V.; Sridharan, V.; Thangavelanthum, R.; Thornton-Pett, M.; Wilson, D. Tetrahedron 1997, 53, 11803. (i) Grigg, R.; Loganathan, V.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S.; Worakun, T. Tetrahedron 1996, 52, 11479. (j) Griggs, R.; Sansano, J. M. Tetrahedron 1996, 52, 13441. (k) Grigg, R.; Sridharan, V.; Xu, L.-H. J. Chem. Soc., Chem. Commun. 1995, 1903. (l) Kimura, M.; Horino, Y.; Wakamiya, Y.; Okajima, T.; Tamaru, Y. J. Am. Chem. Soc. 1997, 119, 10869. (m) Kimura, M.; Wakamiya, Y.; Horino, Y.; Tamaru, Y. Tetrahedron Lett. 1997, 38, 3963. (n) Horino, Y.; Kimura, M.; Wakamiya, Y.; Okajima, T.; Tamaru, Y. Angew. Chem. Int. Ed. 1999, 38, 121. (o) Noguchi, M.; Okada, H.; Wantanabe, M.; Okuda, K.; Nakamura, O. Tetrahedron 1996, 52, 6581. (p) Gericke, R.; Lues, I. Tetrahedron Lett. 1992, 33, 1871. (q) Tanaka, H.; Kameyama, Y.; Sumida, S.; Yamada, T.; Tokumaru, Y.; Shiroi, T.; Sasaoka, M.; Taniguchi, M.; Torri, S. Synlett 1991, 888. (r) Farina, V.; Kant, J. Tetrahedron Lett. 1992, 33, 3563. (s) Farina, V.; Kant, J. Tetrahedron Lett. 1992, 33, 3559. (t) Broggini, G.; Bruché, L.; Zecchi, G. J. Chem. Soc., Perkin Trans. 1 1990, 533. (u) Nilsson, B. M.; Hacksell, U. J. Heterocycl. Chem. 1989, 26, 269. (v) Jones, B. C. N. M.; Silverton, J. V.; Simons, C.; Megati, S.; Nishimura, H.; Maeda, Y.; Mitsuya, H.; Zemlicka, J. J. Med. Chem. 1995, 38, 1397. (w) Rádl, S.; Kovárová, L. Collect. Czech. Chem. Commun. 1991, 56, 2413. (x) For an account on living polymerization of allenamides, see: Takagi, K.; Tomita, I.; Endo, T. Macromolecules 1998, 31, 6741.
33. For highly stereoselective [4+2] cycloaddition reactions of chiral allenamides, see: (a) Wei, L.-L.; Hsung, R. P.; Xiong, H.; Mulder, J. A.; Nkansah, N. T. Org. Lett. 1999, 1, 2145. (b) Wei, L.-L.; Xiong, H.; Douglas, C. J.; Hsung, R. P. Tetrahedron Lett. 1999, 40, 6903.
34. For highly stereoselective [4+2] cycloaddition reactions of chiral allenamides, see: (a) Wei, L.-L.; Hsung, R. P.; Xiong, H.; Mulder, J. A.; Nkansah, N. T. Org. Lett. 1999, 1, 2145. (b) Wei, L.-L.; Xiong, H.; Douglas, C. J.; Hsung, R. P. Tetrahedron Lett. 1999, 40, 6903.
35. For our other studies using chiral allenamides, see: (a) Huang, J.; Xiong, H.; Hsung, R. P.; Rameshkumar, C.; Mulder, J. A.; Grebe, T. P. Org. Lett. 2002, 4, 2417. (b) Rameshkumar, C.; Xiong, H.; Tracey, M. R.; Berry, C. R.; Yao, L. J.; Hsung, R. P. J. Org. Chem. 2002, 67, 1339. (c) Xiong, H.; Hsung, R. P.; Berry, C. R.; Rameshkumar, C. J. Am. Chem. Soc. 2001, 123, 7174. (d) Xiong, H.; Hsung, R. P.; Wei, L.-L.; Berry, C. R.; Mulder, J. A.; Stockwell, B. Org. Lett. 2000, 2, 2869.
36. For our other studies using chiral allenamides, see: (a) Huang, J.; Xiong, H.; Hsung, R. P.; Rameshkumar, C.; Mulder, J. A.; Grebe, T. P. Org. Lett. 2002, 4, 2417. (b) Rameshkumar, C.; Xiong, H.; Tracey, M. R.; Berry, C. R.; Yao, L. J.; Hsung, R. P. J. Org. Chem. 2002, 67, 1339. (c) Xiong, H.; Hsung, R. P.; Berry, C. R.; Rameshkumar, C. J. Am. Chem. Soc. 2001, 123, 7174. (d) Xiong, H.; Hsung, R. P.; Wei, L.-L.; Berry, C. R.; Mulder, J. A.; Stockwell, B. Org. Lett. 2000, 2, 2869.
37. For our other studies using chiral allenamides, see: (a) Huang, J.; Xiong, H.; Hsung, R. P.; Rameshkumar, C.; Mulder, J. A.; Grebe, T. P. Org. Lett. 2002, 4, 2417. (b) Rameshkumar, C.; Xiong, H.; Tracey, M. R.; Berry, C. R.; Yao, L. J.; Hsung, R. P. J. Org. Chem. 2002, 67, 1339. (c) Xiong, H.; Hsung, R. P.; Berry, C. R.; Rameshkumar, C. J. Am. Chem. Soc. 2001, 123, 7174. (d) Xiong, H.; Hsung, R. P.; Wei, L.-L.; Berry, C. R.; Mulder, J. A.; Stockwell, B. Org. Lett. 2000, 2, 2869.
38. For our other studies using chiral allenamides, see: (a) Huang, J.; Xiong, H.; Hsung, R. P.; Rameshkumar, C.; Mulder, J. A.; Grebe, T. P. Org. Lett. 2002, 4, 2417. (b) Rameshkumar, C.; Xiong, H.; Tracey, M. R.; Berry, C. R.; Yao, L. J.; Hsung, R. P. J. Org. Chem. 2002, 67, 1339. (c) Xiong, H.; Hsung, R. P.; Berry, C. R.; Rameshkumar, C. J. Am. Chem. Soc. 2001, 123,
39. For our synthesis of allenamides, see: (a) Wei, L.-L.; Mulder, J. A.; Xiong, H.; Zificsak, C. A.; Douglas, C. J.; Hsung, R. P. Tetrahedron 2001, 57, 459. (b) Xiong, H.; Tracey, M. R.; Grebe, T. P.; Mulder, J. A.; Hsung, R. P. Org. Synth. 2002, in press.
40. For our synthesis of allenamides, see: (a) Wei, L.-L.; Mulder, J. A.; Xiong, H.; Zificsak, C. A.; Douglas, C. J.; Hsung, R. P. Tetrahedron 2001, 57, 459. (b) Xiong, H.; Tracey, M. R.; Grebe, T. P.; Mulder, J. A.; Hsung, R. P. Org. Synth. 2002, in press.
41. For reviews, see: (a) Rappoport, Z. The Chemistry of Enamines, In The Chemistry of Functional Groups; John Wiley and Sons: New York, 1994. (b) Whitesell, J. K.; Whitesell, M. A. Synthesis 1983, 517. (c) Hickmott, P. W. Tetrahedron 1982, 38, 1975. (d) Hickmott, P. W. Tetrahedron 1982, 38, 3363. (e) Lenz, G. R. Synthesis 1978, 489. (f) For cycloadditions using dienamides, see: Campbell, A. L.; Lenz, G. R. Synthesis 1987, 421.
42. For reviews, see: (a) Rappoport, Z. The Chemistry of Enamines, In The Chemistry of Functional Groups; John Wiley and Sons: New York, 1994. (b) Whitesell, J. K.; Whitesell, M. A. Synthesis 1983, 517. (c) Hickmott, P. W. Tetrahedron 1982, 38, 1975. (d) Hickmott, P. W. Tetrahedron 1982, 38, 3363. (e) Lenz, G. R. Synthesis 1978, 489. (f) For cycloadditions using dienamides, see: Campbell, A. L.; Lenz, G. R. Synthesis 1987, 421.
43. For reviews, see: (a) Rappoport, Z. The Chemistry of Enamines, In The Chemistry of Functional Groups; John Wiley and Sons: New York, 1994. (b) Whitesell, J. K.; Whitesell, M. A. Synthesis 1983, 517. (c) Hickmott, P. W. Tetrahedron 1982, 38, 1975. (d) Hickmott, P. W. Tetrahedron 1982, 38, 3363. (e) Lenz, G. R. Synthesis 1978, 489. (f) For cycloadditions using dienamides, see: Campbell, A. L.; Lenz, G. R. Synthesis 1987, 421.
44. For reviews, see: (a) Rappoport, Z. The Chemistry of Enamines, In The Chemistry of Functional Groups; John Wiley and Sons: New York, 1994. (b) Whitesell, J. K.; Whitesell, M. A. Synthesis 1983, 517. (c) Hickmott, P. W. Tetrahedron 1982, 38, 1975. (d) Hickmott, P. W. Tetrahedron 1982, 38, 3363. (e) Lenz, G. R. Synthesis 1978, 489. (f) For cycloadditions using dienamides, see: Campbell, A. L.; Lenz, G. R. Synthesis 1987, 421.
45. For reviews, see: (a) Rappoport, Z. The Chemistry of Enamines, In The Chemistry of Functional Groups; John Wiley and Sons: New York, 1994. (b) Whitesell, J. K.; Whitesell, M. A. Synthesis 1983, 517. (c) Hickmott, P. W. Tetrahedron 1982, 38, 1975. (d) Hickmott, P. W. Tetrahedron 1982, 38, 3363. (e) Lenz, G. R. Synthesis 1978, 489. (f) For cycloadditions using dienamides, see: Campbell, A. L.; Lenz, G. R. Synthesis 1987, 421.
46. For reviews, see: (a) Rappoport, Z. The Chemistry of Enamines, In The Chemistry of Functional Groups; John Wiley and Sons: New York, 1994. (b) Whitesell, J. K.; Whitesell, M. A. Synthesis 1983, 517. (c) Hickmott, P. W. Tetrahedron 1982, 38, 1975. (d) Hickmott, P. W. Tetrahedron 1982, 38, 3363. (e) Lenz, G. R. Synthesis 1978, 489. (f) For cycloadditions using dienamides, see: Campbell, A. L.; Lenz, G. R. Synthesis 1987, 421.
47. For recent studies involving enamides, see: (a) Fuchs, J. R.; Funk, R. L. Org. Lett. 2001, 3, 3349. (b) Maeng, J.-H.; Funk, R. L. Org. Lett. 2000, 3, 1125. (c) Abbiati, G.; Clerici, F.; Gelmi, M. L.; Gambini, A.; Pilati, T. J. Org. Chem. 2001, 66, 6299. (d) Bach, T.; Schröder, J.; Brandl, T.; Hecht, J.; Harms, K. Tetrahedron 1998, 54, 4507. (e) For the only study of epoxidation of achiral enamides, see: Adam, W.; Reinhardt, D.; Reissig, H.-U.; Paulini, K. Tetrahedron 1995, 51, 12257; and references cited therein. (f) See also: Koseki, Y.; Kusano, S.; Ichi, D.; Yoshida, K.; Nagasaka, T. Tetrahedron 2000, 56, 8855.
48. For recent studies involving enamides, see: (a) Fuchs, J. R.; Funk, R. L. Org. Lett. 2001, 3, 3349. (b) Maeng, J.-H.; Funk, R. L. Org. Lett. 2000, 3, 1125. (c) Abbiati, G.; Clerici, F.; Gelmi, M. L.; Gambini, A.; Pilati, T. J. Org. Chem. 2001, 66, 6299. (d) Bach, T.; Schröder, J.; Brandl, T.; Hecht, J.; Harms, K. Tetrahedron 1998, 54, 4507. (e) For the only study of epoxidation of achiral enamides, see: Adam, W.; Reinhardt, D.; Reissig, H.-U.; Paulini, K. Tetrahedron 1995, 51, 12257; and references cited therein. (f) See also: Koseki, Y.; Kusano, S.; Ichi, D.; Yoshida, K.; Nagasaka, T. Tetrahedron 2000, 56, 8855.
49. For recent studies involving enamides, see: (a) Fuchs, J. R.; Funk, R. L. Org. Lett. 2001, 3, 3349. (b) Maeng, J.-H.; Funk, R. L. Org. Lett. 2000, 3, 1125. (c) Abbiati, G.; Clerici, F.; Gelmi, M. L.; Gambini, A.; Pilati, T. J. Org. Chem. 2001, 66, 6299. (d) Bach, T.; Schröder, J.; Brandl, T.; Hecht, J.; Harms, K. Tetrahedron 1998, 54, 4507. (e) For the only study of epoxidation of achiral enamides, see: Adam, W.; Reinhardt, D.; Reissig, H.-U.; Paulini, K. Tetrahedron 1995, 51, 12257; and references cited therein. (f) See also: Koseki, Y.; Kusano, S.; Ichi, D.; Yoshida, K.; Nagasaka, T. Tetrahedron 2000, 56, 8855.
50. For recent studies involving enamides, see: (a) Fuchs, J. R.; Funk, R. L. Org. Lett. 2001, 3, 3349. (b) Maeng, J.-H.; Funk, R. L. Org. Lett. 2000, 3, 1125. (c) Abbiati, G.; Clerici, F.; Gelmi, M. L.; Gambini, A.; Pilati, T. J. Org. Chem. 2001, 66, 6299. (d) Bach, T.; Schröder, J.; Brandl, T.; Hecht, J.; Harms, K. Tetrahedron 1998, 54, 4507. (e) For the only study of epoxidation of achiral enamides, see: Adam, W.; Reinhardt, D.; Reissig, H.-U.; Paulini, K. Tetrahedron 1995, 51, 12257; and references cited therein. (f) See also: Koseki, Y.; Kusano, S.; Ichi, D.; Yoshida, K.; Nagasaka, T. Tetrahedron 2000, 56, 8855.
51. For recent studies involving enamides, see: (a) Fuchs, J. R.; Funk, R. L. Org. Lett. 2001, 3, 3349. (b) Maeng, J.-H.; Funk, R. L. Org. Lett. 2000, 3, 1125. (c) Abbiati, G.; Clerici, F.; Gelmi, M. L.; Gambini, A.; Pilati, T. J. Org. Chem. 2001, 66, 6299. (d) Bach, T.; Schröder, J.; Brandl, T.; Hecht, J.; Harms, K. Tetrahedron 1998, 54, 4507. (e) For the only study of epoxidation of achiral enamides, see: Adam, W.; Reinhardt, D.; Reissig, H.-U.; Paulini, K. Tetrahedron 1995, 51, 12257; and references cited therein. (f) See also: Koseki, Y.; Kusano, S.; Ichi, D.; Yoshida, K.; Nagasaka, T. Tetrahedron 2000, 56, 8855.
52. For recent studies involving enamides, see: (a) Fuchs, J. R.; Funk, R. L. Org. Lett. 2001, 3, 3349. (b) Maeng, J.-H.; Funk, R. L. Org. Lett. 2000, 3, 1125. (c) Abbiati, G.; Clerici, F.; Gelmi, M. L.; Gambini, A.; Pilati, T. J. Org. Chem. 2001, 66, 6299. (d) Bach, T.; Schröder, J.; Brandl, T.; Hecht, J.; Harms, K. Tetrahedron 1998, 54, 4507. (e) For the only study of epoxidation of achiral enamides, see: Adam, W.; Reinhardt, D.; Reissig, H.-U.; Paulini, K. Tetrahedron 1995, 51, 12257; and references cited therein. (f) See also: Koseki, Y.; Kusano, S.; Ichi, D.; Yoshida, K.; Nagasaka, T. Tetrahedron 2000, 56, 8855.
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58. For an example see: (a) Petó, C.; Batta, G.; Györgydeák, Z.; Sztaricskai, F. J. Carbohydr. Chem. 1996, 15, 465. (b) For some examples where removal of an electron deficient anomeric nitrogen substituent led to unraveling of the oxygen heterocycle: Robert, J. J.; Swaminathan, S.; John, M. F.; Shalini, W.; Brain, F. C.; Mark, M. D. J. Am. Chem. Soc. 1993, 115, 9816. (c) Gilbert, S.; Chengzhi, Z.; Sergei, G.; Ronald, S. Tetrahedron Lett. 1995, 36, 6387. (d) Katherine, B.; Eric, T. J. Chem. Soc., Perkin Trans. 1 1998, 737. (e) David, C.; Xe-Sheng, M. Tetrahedron Lett. 1997, 38, 8169.
59. For an example see: (a) Petó, C.; Batta, G.; Györgydeák, Z.; Sztaricskai, F. J. Carbohydr. Chem. 1996, 15, 465. (b) For some examples where removal of an electron deficient anomeric nitrogen substituent led to unraveling of the oxygen heterocycle: Robert, J. J.; Swaminathan, S.; John, M. F.; Shalini, W.; Brain, F. C.; Mark, M. D. J. Am. Chem. Soc. 1993, 115, 9816. (c) Gilbert, S.; Chengzhi, Z.; Sergei, G.; Ronald, S. Tetrahedron Lett. 1995, 36, 6387. (d) Katherine, B.; Eric, T. J. Chem. Soc., Perkin Trans. 1 1998, 737. (e) David, C.; Xe-Sheng, M. Tetrahedron Lett. 1997, 38, 8169.
60. For an example see: (a) Petó, C.; Batta, G.; Györgydeák, Z.; Sztaricskai, F. J. Carbohydr. Chem. 1996, 15, 465. (b) For some examples where removal of an electron deficient anomeric nitrogen substituent led to unraveling of the oxygen heterocycle: Robert, J. J.; Swaminathan, S.; John, M. F.; Shalini, W.; Brain, F. C.; Mark, M. D. J. Am. Chem. Soc. 1993, 115, 9816. (c) Gilbert, S.; Chengzhi, Z.; Sergei, G.; Ronald, S. Tetrahedron Lett. 1995, 36, 6387. (d) Katherine, B.; Eric, T. J. Chem. Soc., Perkin Trans. 1 1998, 737. (e) David, C.; Xe-Sheng, M. Tetrahedron Lett. 1997, 38, 8169.
61. For an example see: (a) Petó, C.; Batta, G.; Györgydeák, Z.; Sztaricskai, F. J. Carbohydr. Chem. 1996, 15, 465. (b) For some examples where removal of an electron deficient anomeric nitrogen substituent led to unraveling of the oxygen heterocycle: Robert, J. J.; Swaminathan, S.; John, M. F.; Shalini, W.; Brain, F. C.; Mark, M. D. J. Am. Chem. Soc. 1993, 115, 9816. (c) Gilbert, S.; Chengzhi, Z.; Sergei, G.; Ronald, S. Tetrahedron Lett. 1995, 36, 6387. (d) Katherine, B.; Eric, T. J. Chem. Soc., Perkin Trans. 1 1998, 737. (e) David, C.; Xe-Sheng, M. Tetrahedron Lett. 1997, 38, 8169.
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75. When substituents at C5 and C6 are trans in these pyranyl heterocycles, we observed strong NOE (see pyrans 21 and 22) between protons at C2 and C3 presumably because these two protons are not necessarily locked in a diaxial relationship unlike those in 20.