Pyranyl heterocycles from inverse electron demand hetero [4+2] cycloaddition reactions of chiral allenamides as a new chiral template for constructing C-glycoside substrates

Synlett

Volumn , Issue 9 SPEC. ISS., 2003, Pages 1241-1246

  Rameshkumar, C ^a   Hsung, Richard P ^a  

^a UNIVERSITY OF MINNESOTA   (United States)

Author keywords

Hydroboration oxidation; Pyranyl heterocycles

Indexed keywords

ALKENE DERIVATIVE; ALLENE DERIVATIVE; GLYCOSIDE; HETEROCYCLIC COMPOUND; PYRAN DERIVATIVE;

ARTICLE; CHIRALITY; CYCLOADDITION; DIHYDROXYLATION; HYDROBORATION; OXIDATION; STEREOCHEMISTRY;

EID: 0037623735     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-40352     Document Type: Article

References (47)

1. A recipient of 2001 Camille Dreyfus Teacher-Scholar Award and McKnight Faculty Award.
2. Berry, C. R.; Rameshkumar, C.; Tracey, M. R.; Wei, L.-L.; Hsung, R. P. Synlett 2003, 791.
3. For reviews on allenes see: (a) Saalfrank, R. W.; Lurz, C. J. In Methoden der organischen Chemie (Houben-Weyl); 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 Methoden der organischen Chemie (Houben-Weyl); 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 Methoden der organischen Chemie (Houben-Weyl); 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 Methoden der organischen Chemie (Houben-Weyl); 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 Methoden der organischen Chemie (Houben-Weyl); 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 Methoden der organischen Chemie (Houben-Weyl); 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 reviews on allenes see: (a) Saalfrank, R. W.; Lurz, C. J. In Methoden der organischen Chemie (Houben-Weyl); 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.
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. (1) 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. (1) 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. (1) 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. (1) 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. (1) 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. (1) 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. (1) 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. (1) 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. (1) 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. (1) 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. (1) 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 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.
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 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.
36. For our other studies using chiral allenamides, see: (a) Huang, J.; Xiong, H.; Hsung, R. P.; Rameshkumar, C.; Mulder, J. A.; G rebe, 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.; G rebe, 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.; G rebe, 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.
39. For our other studies using chiral allenamides, see: (a) Huang, J.; Xiong, H.; Hsung, R. P.; Rameshkumar, C.; Mulder, J. A.; G rebe, 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.
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., 2003, accepted.
41. 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., 2003, accepted.
42. (a) Postema, M. H. D. Tetrahedron 1992, 48, 8545.
43. (b) Postema, M. H. D. C-Glycoside Synthesis; CRC Press: Ann Arbor, 1995.
44. (c) Levy, D. E.; Tang, C. The Chemistry of C-Glycosides, 1st ed., Vol. 13; Pergamon Press: Oxford, 1995.
45. Parker, K. A. Pure Appl. Chem. 1994, 66, 2135.
46. For selected experimental procedures and characterizations: see abstract
47. When substituents at C5 and C6 are trans in these pyranyl heterocycles such as 21, we observed strong NOE between protons at C2 and C3 presumably because these two protons are not necessarily locked in di-axial relationship unlike those in pyrans where C5 and C6 substituents are cis.