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Volumn 44, Issue 20, 2003, Pages 3905-3909

The hetero-Diels-Alder addition of ethyl 2-nitrosoacrylate to electron-rich alkenes as a route to unnatural α-amino acids

Author keywords

Allylsilanes; Enamines; Enol ethers; Ethyl 2 nitrosoacrylate; Hetero Diels Alder addition; amino acids

Indexed keywords

ACRYLIC ACID DERIVATIVE; ALKENE DERIVATIVE; ALLYL COMPOUND; ALPHA AMINO ACID; ENAMINE; ETHER DERIVATIVE; ETHYL 2 NITROSOACRYLATE; OXAZINE DERIVATIVE; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0037433833     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00836-0     Document Type: Article
Times cited : (43)

References (69)
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    • For selected reviews, see: (a) Altenbach, H.-J. In Organic Synthesis Highlights; Mulzer, J.; Altenbach, H.-J.; Braun, M.; Krohn, K.; Reissig, H.-U., Eds.; VCH: Weinheim, 1991; pp. 300-305; (b) Cintas, P. Tetrahedron 1991, 47, 6079-6111; (c) Ohfune, Y. Acc. Chem. Res. 1992, 25, 360-366; (d) Williams, R. M.; Hendrix, J. A. Chem. Rev. 1992, 92, 889-917; (e) Duthaler, R. O. Tetrahedron 1994, 50, 1539-1650; (f) Hanessian, S.; McNaughton-Smith, G.; Lombart, H.-G.; Lubell, W. D. Tetrahedron 1997, 53, 12789-12854; (g) Cativiela, C.; Díaz-de-Villegas, M. D. Tetrahedron: Asymmetry 1998, 9, 3517-3599; (h) Abellán, T.; Chinchilla, R.; Galindo, N.; Nájera, C.; Sansano, J. M. J. Heterocyclic Chem. 2000, 37, 467-479; (i) Abellán, T.; Chinchilla, R.; Galindo, N.; Guillena, G.; Nájera, C.; Sansano, J. M. Eur. J. Org. Chem. 2000, 2689-2697; (j) Rutjes, F. P. J. T.; Wolf, L. B.; Schoemaker J. Chem. Soc., Perkin Trans. 1 2000, 4197-4212; (k) O'Donnell, M. Aldrichim. Acta 2001, 34, 3-15; (l) Nájera, C. Synlett 2002, 1388-1402; (m) Park, K.-H.; Kurth, M. J. Tetrahedron 2002, 58, 8629-8659.
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    • For selected reviews, see: (a) Altenbach, H.-J. In Organic Synthesis Highlights; Mulzer, J.; Altenbach, H.-J.; Braun, M.; Krohn, K.; Reissig, H.-U., Eds.; VCH: Weinheim, 1991; pp. 300-305; (b) Cintas, P. Tetrahedron 1991, 47, 6079-6111; (c) Ohfune, Y. Acc. Chem. Res. 1992, 25, 360-366; (d) Williams, R. M.; Hendrix, J. A. Chem. Rev. 1992, 92, 889-917; (e) Duthaler, R. O. Tetrahedron 1994, 50, 1539-1650; (f) Hanessian, S.; McNaughton-Smith, G.; Lombart, H.-G.; Lubell, W. D. Tetrahedron 1997, 53, 12789-12854; (g) Cativiela, C.; Díaz-de-Villegas, M. D. Tetrahedron: Asymmetry 1998, 9, 3517-3599; (h) Abellán, T.; Chinchilla, R.; Galindo, N.; Nájera, C.; Sansano, J. M. J. Heterocyclic Chem. 2000, 37, 467-479; (i) Abellán, T.; Chinchilla, R.; Galindo, N.; Guillena, G.; Nájera, C.; Sansano, J. M. Eur. J. Org. Chem. 2000, 2689-2697; (j) Rutjes, F. P. J. T.; Wolf, L. B.; Schoemaker J. Chem. Soc., Perkin Trans. 1 2000, 4197-4212; (k) O'Donnell, M. Aldrichim. Acta 2001, 34, 3-15; (l) Nájera, C. Synlett 2002, 1388-1402; (m) Park, K.-H.; Kurth, M. J. Tetrahedron 2002, 58, 8629-8659.
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    • For selected reviews, see: (a) Altenbach, H.-J. In Organic Synthesis Highlights; Mulzer, J.; Altenbach, H.-J.; Braun, M.; Krohn, K.; Reissig, H.-U., Eds.; VCH: Weinheim, 1991; pp. 300-305; (b) Cintas, P. Tetrahedron 1991, 47, 6079-6111; (c) Ohfune, Y. Acc. Chem. Res. 1992, 25, 360-366; (d) Williams, R. M.; Hendrix, J. A. Chem. Rev. 1992, 92, 889-917; (e) Duthaler, R. O. Tetrahedron 1994, 50, 1539-1650; (f) Hanessian, S.; McNaughton-Smith, G.; Lombart, H.-G.; Lubell, W. D. Tetrahedron 1997, 53, 12789-12854; (g) Cativiela, C.; Díaz-de-Villegas, M. D. Tetrahedron: Asymmetry 1998, 9, 3517-3599; (h) Abellán, T.; Chinchilla, R.; Galindo, N.; Nájera, C.; Sansano, J. M. J. Heterocyclic Chem. 2000, 37, 467-479; (i) Abellán, T.; Chinchilla, R.; Galindo, N.; Guillena, G.; Nájera, C.; Sansano, J. M. Eur. J. Org. Chem. 2000, 2689-2697; (j) Rutjes, F. P. J. T.; Wolf, L. B.; Schoemaker J. Chem. Soc., Perkin Trans. 1 2000, 4197-4212; (k) O'Donnell, M. Aldrichim. Acta 2001, 34, 3-15; (l) Nájera, C. Synlett 2002, 1388-1402; (m) Park, K.-H.; Kurth, M. J. Tetrahedron 2002, 58, 8629-8659.
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    • For selected reviews, see: (a) Altenbach, H.-J. In Organic Synthesis Highlights; Mulzer, J.; Altenbach, H.-J.; Braun, M.; Krohn, K.; Reissig, H.-U., Eds.; VCH: Weinheim, 1991; pp. 300-305; (b) Cintas, P. Tetrahedron 1991, 47, 6079-6111; (c) Ohfune, Y. Acc. Chem. Res. 1992, 25, 360-366; (d) Williams, R. M.; Hendrix, J. A. Chem. Rev. 1992, 92, 889-917; (e) Duthaler, R. O. Tetrahedron 1994, 50, 1539-1650; (f) Hanessian, S.; McNaughton-Smith, G.; Lombart, H.-G.; Lubell, W. D. Tetrahedron 1997, 53, 12789-12854; (g) Cativiela, C.; Díaz-de-Villegas, M. D. Tetrahedron: Asymmetry 1998, 9, 3517-3599; (h) Abellán, T.; Chinchilla, R.; Galindo, N.; Nájera, C.; Sansano, J. M. J. Heterocyclic Chem. 2000, 37, 467-479; (i) Abellán, T.; Chinchilla, R.; Galindo, N.; Guillena, G.; Nájera, C.; Sansano, J. M. Eur. J. Org. Chem. 2000, 2689-2697; (j) Rutjes, F. P. J. T.; Wolf, L. B.; Schoemaker J. Chem. Soc., Perkin Trans. 1 2000, 4197-4212; (k) O'Donnell, M. Aldrichim. Acta 2001, 34, 3-15; (l) Nájera, C. Synlett 2002, 1388-1402; (m) Park, K.-H.; Kurth, M. J. Tetrahedron 2002, 58, 8629-8659.
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    • For selected reviews, see: (a) Altenbach, H.-J. In Organic Synthesis Highlights; Mulzer, J.; Altenbach, H.-J.; Braun, M.; Krohn, K.; Reissig, H.-U., Eds.; VCH: Weinheim, 1991; pp. 300-305; (b) Cintas, P. Tetrahedron 1991, 47, 6079-6111; (c) Ohfune, Y. Acc. Chem. Res. 1992, 25, 360-366; (d) Williams, R. M.; Hendrix, J. A. Chem. Rev. 1992, 92, 889-917; (e) Duthaler, R. O. Tetrahedron 1994, 50, 1539-1650; (f) Hanessian, S.; McNaughton-Smith, G.; Lombart, H.-G.; Lubell, W. D. Tetrahedron 1997, 53, 12789-12854; (g) Cativiela, C.; Díaz-de-Villegas, M. D. Tetrahedron: Asymmetry 1998, 9, 3517-3599; (h) Abellán, T.; Chinchilla, R.; Galindo, N.; Nájera, C.; Sansano, J. M. J. Heterocyclic Chem. 2000, 37, 467-479; (i) Abellán, T.; Chinchilla, R.; Galindo, N.; Guillena, G.; Nájera, C.; Sansano, J. M. Eur. J. Org. Chem. 2000, 2689-2697; (j) Rutjes, F. P. J. T.; Wolf, L. B.; Schoemaker J. Chem. Soc., Perkin Trans. 1 2000, 4197-4212; (k) O'Donnell, M. Aldrichim. Acta 2001, 34, 3-15; (l) Nájera, C. Synlett 2002, 1388-1402; (m) Park, K.-H.; Kurth, M. J. Tetrahedron 2002, 58, 8629-8659.
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    • (2002) Tetrahedron , vol.58 , pp. 8629-8659
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    • For selected recent publications, see: (a) Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445-446; (b) Kimura, T.; Vassilev, V. P.; Shen, G.-J.; Wong, C.-H. J. Am. Chem. Soc. 1997, 119, 11734-11742; (c) Kokotos, G.; Padrón, J. M.; Martín, T.; Gibbons, W. A.; Martín, V. S. J. Org. Chem. 1998, 63, 3741-3744; (d) Sibi, M. P.; Rutherford, D.; Renhowe, P. A.; Li, B. J. Am. Chem. Soc. 1999, 121, 7509-7516; (e) Ishitani, H.; Komiyama, S.; Hasegawa, Y.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 762-766; (f) Saaby, S.; Fang, X.; Gathergood, N.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2000, 39, 4114-4116; (g) Sabat, M.; Jonson, C. R. Org. Lett. 2000, 2, 1089-1092; (h) Collier, P. N.; Campbell, A. D.; Patel, I.; Taylor, R. J. K. Tetrahedron Lett. 2000, 41, 7115-7119; (i) Yao, S.; Saaby, S.; Hazell, R. G.; Jørgensen, K. A. Chem. Eur. J. 2000, 6, 2435-2448; (j) Atfani, M.; Wei, L.; Lubell, W. D. Org. Lett. 2001, 3, 2965-2968; (k) Cordova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, III, C. F. J. Am. Chem. Soc. 2002, 124, 1842-1843; (l) Cordova, A.; Watanabe, S.; Tanaka, F.; Notz, W.; Barbas, III, C. F. J. Am. Chem. Soc. 2002, 124, 1866-1867; (m) Markidis, T.; Kokotos, G. J. Org. Chem. 2002, 67, 1685-1688; (n) Collier, P. N.; Campbell, A. D.; Patel, I.; Raynham, T. M.; Taylor, R. J. K. J. Org. Chem. 2002, 67, 1802-1815; (o) Collier, P. N.; Campbell, A. D.; Patel, I.; Taylor, R. J. K. Tetrahedron 2002, 58, 6117-6125.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 445-446
    • Petasis, N.A.1    Zavialov, I.A.2
  • 15
    • 0031436952 scopus 로고    scopus 로고
    • For selected recent publications, see: (a) Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445-446; (b) Kimura, T.; Vassilev, V. P.; Shen, G.-J.; Wong, C.-H. J. Am. Chem. Soc. 1997, 119, 11734-11742; (c) Kokotos, G.; Padrón, J. M.; Martín, T.; Gibbons, W. A.; Martín, V. S. J. Org. Chem. 1998, 63, 3741-3744; (d) Sibi, M. P.; Rutherford, D.; Renhowe, P. A.; Li, B. J. Am. Chem. Soc. 1999, 121, 7509-7516; (e) Ishitani, H.; Komiyama, S.; Hasegawa, Y.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 762-766; (f) Saaby, S.; Fang, X.; Gathergood, N.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2000, 39, 4114-4116; (g) Sabat, M.; Jonson, C. R. Org. Lett. 2000, 2, 1089-1092; (h) Collier, P. N.; Campbell, A. D.; Patel, I.; Taylor, R. J. K. Tetrahedron Lett. 2000, 41, 7115-7119; (i) Yao, S.; Saaby, S.; Hazell, R. G.; Jørgensen, K. A. Chem. Eur. J. 2000, 6, 2435-2448; (j) Atfani, M.; Wei, L.; Lubell, W. D. Org. Lett. 2001, 3, 2965-2968; (k) Cordova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, III, C. F. J. Am. Chem. Soc. 2002, 124, 1842-1843; (l) Cordova, A.; Watanabe, S.; Tanaka, F.; Notz, W.; Barbas, III, C. F. J. Am. Chem. Soc. 2002, 124, 1866-1867; (m) Markidis, T.; Kokotos, G. J. Org. Chem. 2002, 67, 1685-1688; (n) Collier, P. N.; Campbell, A. D.; Patel, I.; Raynham, T. M.; Taylor, R. J. K. J. Org. Chem. 2002, 67, 1802-1815; (o) Collier, P. N.; Campbell, A. D.; Patel, I.; Taylor, R. J. K. Tetrahedron 2002, 58, 6117-6125.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 11734-11742
    • Kimura, T.1    Vassilev, V.P.2    Shen, G.-J.3    Wong, C.-H.4
  • 16
    • 0001340433 scopus 로고    scopus 로고
    • For selected recent publications, see: (a) Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445-446; (b) Kimura, T.; Vassilev, V. P.; Shen, G.-J.; Wong, C.-H. J. Am. Chem. Soc. 1997, 119, 11734-11742; (c) Kokotos, G.; Padrón, J. M.; Martín, T.; Gibbons, W. A.; Martín, V. S. J. Org. Chem. 1998, 63, 3741-3744; (d) Sibi, M. P.; Rutherford, D.; Renhowe, P. A.; Li, B. J. Am. Chem. Soc. 1999, 121, 7509-7516; (e) Ishitani, H.; Komiyama, S.; Hasegawa, Y.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 762-766; (f) Saaby, S.; Fang, X.; Gathergood, N.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2000, 39, 4114-4116; (g) Sabat, M.; Jonson, C. R. Org. Lett. 2000, 2, 1089-1092; (h) Collier, P. N.; Campbell, A. D.; Patel, I.; Taylor, R. J. K. Tetrahedron Lett. 2000, 41, 7115-7119; (i) Yao, S.; Saaby, S.; Hazell, R. G.; Jørgensen, K. A. Chem. Eur. J. 2000, 6, 2435-2448; (j) Atfani, M.; Wei, L.; Lubell, W. D. Org. Lett. 2001, 3, 2965-2968; (k) Cordova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, III, C. F. J. Am. Chem. Soc. 2002, 124, 1842-1843; (l) Cordova, A.; Watanabe, S.; Tanaka, F.; Notz, W.; Barbas, III, C. F. J. Am. Chem. Soc. 2002, 124, 1866-1867; (m) Markidis, T.; Kokotos, G. J. Org. Chem. 2002, 67, 1685-1688; (n) Collier, P. N.; Campbell, A. D.; Patel, I.; Raynham, T. M.; Taylor, R. J. K. J. Org. Chem. 2002, 67, 1802-1815; (o) Collier, P. N.; Campbell, A. D.; Patel, I.; Taylor, R. J. K. Tetrahedron 2002, 58, 6117-6125.
    • (1998) J. Org. Chem. , vol.63 , pp. 3741-3744
    • Kokotos, G.1    Padrón, J.M.2    Martín, T.3    Gibbons, W.4    Martín, V.S.5
  • 17
    • 0033603875 scopus 로고    scopus 로고
    • For selected recent publications, see: (a) Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445-446; (b) Kimura, T.; Vassilev, V. P.; Shen, G.-J.; Wong, C.-H. J. Am. Chem. Soc. 1997, 119, 11734-11742; (c) Kokotos, G.; Padrón, J. M.; Martín, T.; Gibbons, W. A.; Martín, V. S. J. Org. Chem. 1998, 63, 3741-3744; (d) Sibi, M. P.; Rutherford, D.; Renhowe, P. A.; Li, B. J. Am. Chem. Soc. 1999, 121, 7509-7516; (e) Ishitani, H.; Komiyama, S.; Hasegawa, Y.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 762-766; (f) Saaby, S.; Fang, X.; Gathergood, N.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2000, 39, 4114-4116; (g) Sabat, M.; Jonson, C. R. Org. Lett. 2000, 2, 1089-1092; (h) Collier, P. N.; Campbell, A. D.; Patel, I.; Taylor, R. J. K. Tetrahedron Lett. 2000, 41, 7115-7119; (i) Yao, S.; Saaby, S.; Hazell, R. G.; Jørgensen, K. A. Chem. Eur. J. 2000, 6, 2435-2448; (j) Atfani, M.; Wei, L.; Lubell, W. D. Org. Lett. 2001, 3, 2965-2968; (k) Cordova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, III, C. F. J. Am. Chem. Soc. 2002, 124, 1842-1843; (l) Cordova, A.; Watanabe, S.; Tanaka, F.; Notz, W.; Barbas, III, C. F. J. Am. Chem. Soc. 2002, 124, 1866-1867; (m) Markidis, T.; Kokotos, G. J. Org. Chem. 2002, 67, 1685-1688; (n) Collier, P. N.; Campbell, A. D.; Patel, I.; Raynham, T. M.; Taylor, R. J. K. J. Org. Chem. 2002, 67, 1802-1815; (o) Collier, P. N.; Campbell, A. D.; Patel, I.; Taylor, R. J. K. Tetrahedron 2002, 58, 6117-6125.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 7509-7516
    • Sibi, M.P.1    Rutherford, D.2    Renhowe, P.A.3    Li, B.4
  • 18
    • 0034624418 scopus 로고    scopus 로고
    • For selected recent publications, see: (a) Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445-446; (b) Kimura, T.; Vassilev, V. P.; Shen, G.-J.; Wong, C.-H. J. Am. Chem. Soc. 1997, 119, 11734-11742; (c) Kokotos, G.; Padrón, J. M.; Martín, T.; Gibbons, W. A.; Martín, V. S. J. Org. Chem. 1998, 63, 3741-3744; (d) Sibi, M. P.; Rutherford, D.; Renhowe, P. A.; Li, B. J. Am. Chem. Soc. 1999, 121, 7509-7516; (e) Ishitani, H.; Komiyama, S.; Hasegawa, Y.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 762-766; (f) Saaby, S.; Fang, X.; Gathergood, N.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2000, 39, 4114-4116; (g) Sabat, M.; Jonson, C. R. Org. Lett. 2000, 2, 1089-1092; (h) Collier, P. N.; Campbell, A. D.; Patel, I.; Taylor, R. J. K. Tetrahedron Lett. 2000, 41, 7115-7119; (i) Yao, S.; Saaby, S.; Hazell, R. G.; Jørgensen, K. A. Chem. Eur. J. 2000, 6, 2435-2448; (j) Atfani, M.; Wei, L.; Lubell, W. D. Org. Lett. 2001, 3, 2965-2968; (k) Cordova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, III, C. F. J. Am. Chem. Soc. 2002, 124, 1842-1843; (l) Cordova, A.; Watanabe, S.; Tanaka, F.; Notz, W.; Barbas, III, C. F. J. Am. Chem. Soc. 2002, 124, 1866-1867; (m) Markidis, T.; Kokotos, G. J. Org. Chem. 2002, 67, 1685-1688; (n) Collier, P. N.; Campbell, A. D.; Patel, I.; Raynham, T. M.; Taylor, R. J. K. J. Org. Chem. 2002, 67, 1802-1815; (o) Collier, P. N.; Campbell, A. D.; Patel, I.; Taylor, R. J. K. Tetrahedron 2002, 58, 6117-6125.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 762-766
    • Ishitani, H.1    Komiyama, S.2    Hasegawa, Y.3    Kobayashi, S.4
  • 19
    • 42749097458 scopus 로고    scopus 로고
    • For selected recent publications, see: (a) Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445-446; (b) Kimura, T.; Vassilev, V. P.; Shen, G.-J.; Wong, C.-H. J. Am. Chem. Soc. 1997, 119, 11734-11742; (c) Kokotos, G.; Padrón, J. M.; Martín, T.; Gibbons, W. A.; Martín, V. S. J. Org. Chem. 1998, 63, 3741-3744; (d) Sibi, M. P.; Rutherford, D.; Renhowe, P. A.; Li, B. J. Am. Chem. Soc. 1999, 121, 7509-7516; (e) Ishitani, H.; Komiyama, S.; Hasegawa, Y.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 762-766; (f) Saaby, S.; Fang, X.; Gathergood, N.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2000, 39, 4114-4116; (g) Sabat, M.; Jonson, C. R. Org. Lett. 2000, 2, 1089-1092; (h) Collier, P. N.; Campbell, A. D.; Patel, I.; Taylor, R. J. K. Tetrahedron Lett. 2000, 41, 7115-7119; (i) Yao, S.; Saaby, S.; Hazell, R. G.; Jørgensen, K. A. Chem. Eur. J. 2000, 6, 2435-2448; (j) Atfani, M.; Wei, L.; Lubell, W. D. Org. Lett. 2001, 3, 2965-2968; (k) Cordova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, III, C. F. J. Am. Chem. Soc. 2002, 124, 1842-1843; (l) Cordova, A.; Watanabe, S.; Tanaka, F.; Notz, W.; Barbas, III, C. F. J. Am. Chem. Soc. 2002, 124, 1866-1867; (m) Markidis, T.; Kokotos, G. J. Org. Chem. 2002, 67, 1685-1688; (n) Collier, P. N.; Campbell, A. D.; Patel, I.; Raynham, T. M.; Taylor, R. J. K. J. Org. Chem. 2002, 67, 1802-1815; (o) Collier, P. N.; Campbell, A. D.; Patel, I.; Taylor, R. J. K. Tetrahedron 2002, 58, 6117-6125.
    • (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 4114-4116
    • Saaby, S.1    Fang, X.2    Gathergood, N.3    Jørgensen, K.A.4
  • 20
    • 0034689857 scopus 로고    scopus 로고
    • For selected recent publications, see: (a) Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445-446; (b) Kimura, T.; Vassilev, V. P.; Shen, G.-J.; Wong, C.-H. J. Am. Chem. Soc. 1997, 119, 11734-11742; (c) Kokotos, G.; Padrón, J. M.; Martín, T.; Gibbons, W. A.; Martín, V. S. J. Org. Chem. 1998, 63, 3741-3744; (d) Sibi, M. P.; Rutherford, D.; Renhowe, P. A.; Li, B. J. Am. Chem. Soc. 1999, 121, 7509-7516; (e) Ishitani, H.; Komiyama, S.; Hasegawa, Y.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 762-766; (f) Saaby, S.; Fang, X.; Gathergood, N.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2000, 39, 4114-4116; (g) Sabat, M.; Jonson, C. R. Org. Lett. 2000, 2, 1089-1092; (h) Collier, P. N.; Campbell, A. D.; Patel, I.; Taylor, R. J. K. Tetrahedron Lett. 2000, 41, 7115-7119; (i) Yao, S.; Saaby, S.; Hazell, R. G.; Jørgensen, K. A. Chem. Eur. J. 2000, 6, 2435-2448; (j) Atfani, M.; Wei, L.; Lubell, W. D. Org. Lett. 2001, 3, 2965-2968; (k) Cordova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, III, C. F. J. Am. Chem. Soc. 2002, 124, 1842-1843; (l) Cordova, A.; Watanabe, S.; Tanaka, F.; Notz, W.; Barbas, III, C. F. J. Am. Chem. Soc. 2002, 124, 1866-1867; (m) Markidis, T.; Kokotos, G. J. Org. Chem. 2002, 67, 1685-1688; (n) Collier, P. N.; Campbell, A. D.; Patel, I.; Raynham, T. M.; Taylor, R. J. K. J. Org. Chem. 2002, 67, 1802-1815; (o) Collier, P. N.; Campbell, A. D.; Patel, I.; Taylor, R. J. K. Tetrahedron 2002, 58, 6117-6125.
    • (2000) Org. Lett. , vol.2 , pp. 1089-1092
    • Sabat, M.1    Jonson, C.R.2
  • 21
    • 0034596431 scopus 로고    scopus 로고
    • For selected recent publications, see: (a) Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445-446; (b) Kimura, T.; Vassilev, V. P.; Shen, G.-J.; Wong, C.-H. J. Am. Chem. Soc. 1997, 119, 11734-11742; (c) Kokotos, G.; Padrón, J. M.; Martín, T.; Gibbons, W. A.; Martín, V. S. J. Org. Chem. 1998, 63, 3741-3744; (d) Sibi, M. P.; Rutherford, D.; Renhowe, P. A.; Li, B. J. Am. Chem. Soc. 1999, 121, 7509-7516; (e) Ishitani, H.; Komiyama, S.; Hasegawa, Y.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 762-766; (f) Saaby, S.; Fang, X.; Gathergood, N.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2000, 39, 4114-4116; (g) Sabat, M.; Jonson, C. R. Org. Lett. 2000, 2, 1089-1092; (h) Collier, P. N.; Campbell, A. D.; Patel, I.; Taylor, R. J. K. Tetrahedron Lett. 2000, 41, 7115-7119; (i) Yao, S.; Saaby, S.; Hazell, R. G.; Jørgensen, K. A. Chem. Eur. J. 2000, 6, 2435-2448; (j) Atfani, M.; Wei, L.; Lubell, W. D. Org. Lett. 2001, 3, 2965-2968; (k) Cordova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, III, C. F. J. Am. Chem. Soc. 2002, 124, 1842-1843; (l) Cordova, A.; Watanabe, S.; Tanaka, F.; Notz, W.; Barbas, III, C. F. J. Am. Chem. Soc. 2002, 124, 1866-1867; (m) Markidis, T.; Kokotos, G. J. Org. Chem. 2002, 67, 1685-1688; (n) Collier, P. N.; Campbell, A. D.; Patel, I.; Raynham, T. M.; Taylor, R. J. K. J. Org. Chem. 2002, 67, 1802-1815; (o) Collier, P. N.; Campbell, A. D.; Patel, I.; Taylor, R. J. K. Tetrahedron 2002, 58, 6117-6125.
    • (2000) Tetrahedron Lett. , vol.41 , pp. 7115-7119
    • Collier, P.N.1    Campbell, A.D.2    Patel, I.3    Taylor, R.J.K.4
  • 22
    • 0034600913 scopus 로고    scopus 로고
    • For selected recent publications, see: (a) Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445-446; (b) Kimura, T.; Vassilev, V. P.; Shen, G.-J.; Wong, C.-H. J. Am. Chem. Soc. 1997, 119, 11734-11742; (c) Kokotos, G.; Padrón, J. M.; Martín, T.; Gibbons, W. A.; Martín, V. S. J. Org. Chem. 1998, 63, 3741-3744; (d) Sibi, M. P.; Rutherford, D.; Renhowe, P. A.; Li, B. J. Am. Chem. Soc. 1999, 121, 7509-7516; (e) Ishitani, H.; Komiyama, S.; Hasegawa, Y.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 762-766; (f) Saaby, S.; Fang, X.; Gathergood, N.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2000, 39, 4114-4116; (g) Sabat, M.; Jonson, C. R. Org. Lett. 2000, 2, 1089-1092; (h) Collier, P. N.; Campbell, A. D.; Patel, I.; Taylor, R. J. K. Tetrahedron Lett. 2000, 41, 7115-7119; (i) Yao, S.; Saaby, S.; Hazell, R. G.; Jørgensen, K. A. Chem. Eur. J. 2000, 6, 2435-2448; (j) Atfani, M.; Wei, L.; Lubell, W. D. Org. Lett. 2001, 3, 2965-2968; (k) Cordova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, III, C. F. J. Am. Chem. Soc. 2002, 124, 1842-1843; (l) Cordova, A.; Watanabe, S.; Tanaka, F.; Notz, W.; Barbas, III, C. F. J. Am. Chem. Soc. 2002, 124, 1866-1867; (m) Markidis, T.; Kokotos, G. J. Org. Chem. 2002, 67, 1685-1688; (n) Collier, P. N.; Campbell, A. D.; Patel, I.; Raynham, T. M.; Taylor, R. J. K. J. Org. Chem. 2002, 67, 1802-1815; (o) Collier, P. N.; Campbell, A. D.; Patel, I.; Taylor, R. J. K. Tetrahedron 2002, 58, 6117-6125.
    • (2000) Chem. Eur. J. , vol.6 , pp. 2435-2448
    • Yao, S.1    Saaby, S.2    Hazell, R.G.3    Jørgensen, K.A.4
  • 23
    • 0001019960 scopus 로고    scopus 로고
    • For selected recent publications, see: (a) Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445-446; (b) Kimura, T.; Vassilev, V. P.; Shen, G.-J.; Wong, C.-H. J. Am. Chem. Soc. 1997, 119, 11734-11742; (c) Kokotos, G.; Padrón, J. M.; Martín, T.; Gibbons, W. A.; Martín, V. S. J. Org. Chem. 1998, 63, 3741-3744; (d) Sibi, M. P.; Rutherford, D.; Renhowe, P. A.; Li, B. J. Am. Chem. Soc. 1999, 121, 7509-7516; (e) Ishitani, H.; Komiyama, S.; Hasegawa, Y.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 762-766; (f) Saaby, S.; Fang, X.; Gathergood, N.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2000, 39, 4114-4116; (g) Sabat, M.; Jonson, C. R. Org. Lett. 2000, 2, 1089-1092; (h) Collier, P. N.; Campbell, A. D.; Patel, I.; Taylor, R. J. K. Tetrahedron Lett. 2000, 41, 7115-7119; (i) Yao, S.; Saaby, S.; Hazell, R. G.; Jørgensen, K. A. Chem. Eur. J. 2000, 6, 2435-2448; (j) Atfani, M.; Wei, L.; Lubell, W. D. Org. Lett. 2001, 3, 2965-2968; (k) Cordova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, III, C. F. J. Am. Chem. Soc. 2002, 124, 1842-1843; (l) Cordova, A.; Watanabe, S.; Tanaka, F.; Notz, W.; Barbas, III, C. F. J. Am. Chem. Soc. 2002, 124, 1866-1867; (m) Markidis, T.; Kokotos, G. J. Org. Chem. 2002, 67, 1685-1688; (n) Collier, P. N.; Campbell, A. D.; Patel, I.; Raynham, T. M.; Taylor, R. J. K. J. Org. Chem. 2002, 67, 1802-1815; (o) Collier, P. N.; Campbell, A. D.; Patel, I.; Taylor, R. J. K. Tetrahedron 2002, 58, 6117-6125.
    • (2001) Org. Lett. , vol.3 , pp. 2965-2968
    • Atfani, M.1    Wei, L.2    Lubell, W.D.3
  • 24
    • 0037028924 scopus 로고    scopus 로고
    • For selected recent publications, see: (a) Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445-446; (b) Kimura, T.; Vassilev, V. P.; Shen, G.-J.; Wong, C.-H. J. Am. Chem. Soc. 1997, 119, 11734-11742; (c) Kokotos, G.; Padrón, J. M.; Martín, T.; Gibbons, W. A.; Martín, V. S. J. Org. Chem. 1998, 63, 3741-3744; (d) Sibi, M. P.; Rutherford, D.; Renhowe, P. A.; Li, B. J. Am. Chem. Soc. 1999, 121, 7509-7516; (e) Ishitani, H.; Komiyama, S.; Hasegawa, Y.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 762-766; (f) Saaby, S.; Fang, X.; Gathergood, N.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2000, 39, 4114-4116; (g) Sabat, M.; Jonson, C. R. Org. Lett. 2000, 2, 1089-1092; (h) Collier, P. N.; Campbell, A. D.; Patel, I.; Taylor, R. J. K. Tetrahedron Lett. 2000, 41, 7115-7119; (i) Yao, S.; Saaby, S.; Hazell, R. G.; Jørgensen, K. A. Chem. Eur. J. 2000, 6, 2435-2448; (j) Atfani, M.; Wei, L.; Lubell, W. D. Org. Lett. 2001, 3, 2965-2968; (k) Cordova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, III, C. F. J. Am. Chem. Soc. 2002, 124, 1842-1843; (l) Cordova, A.; Watanabe, S.; Tanaka, F.; Notz, W.; Barbas, III, C. F. J. Am. Chem. Soc. 2002, 124, 1866-1867; (m) Markidis, T.; Kokotos, G. J. Org. Chem. 2002, 67, 1685-1688; (n) Collier, P. N.; Campbell, A. D.; Patel, I.; Raynham, T. M.; Taylor, R. J. K. J. Org. Chem. 2002, 67, 1802-1815; (o) Collier, P. N.; Campbell, A. D.; Patel, I.; Taylor, R. J. K. Tetrahedron 2002, 58, 6117-6125.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 1842-1843
    • Cordova, A.1    Notz, W.2    Zhong, G.3    Betancort, J.M.4    Barbas C.F. III5
  • 25
    • 0037028990 scopus 로고    scopus 로고
    • For selected recent publications, see: (a) Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445-446; (b) Kimura, T.; Vassilev, V. P.; Shen, G.-J.; Wong, C.-H. J. Am. Chem. Soc. 1997, 119, 11734-11742; (c) Kokotos, G.; Padrón, J. M.; Martín, T.; Gibbons, W. A.; Martín, V. S. J. Org. Chem. 1998, 63, 3741-3744; (d) Sibi, M. P.; Rutherford, D.; Renhowe, P. A.; Li, B. J. Am. Chem. Soc. 1999, 121, 7509-7516; (e) Ishitani, H.; Komiyama, S.; Hasegawa, Y.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 762-766; (f) Saaby, S.; Fang, X.; Gathergood, N.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2000, 39, 4114-4116; (g) Sabat, M.; Jonson, C. R. Org. Lett. 2000, 2, 1089-1092; (h) Collier, P. N.; Campbell, A. D.; Patel, I.; Taylor, R. J. K. Tetrahedron Lett. 2000, 41, 7115-7119; (i) Yao, S.; Saaby, S.; Hazell, R. G.; Jørgensen, K. A. Chem. Eur. J. 2000, 6, 2435-2448; (j) Atfani, M.; Wei, L.; Lubell, W. D. Org. Lett. 2001, 3, 2965-2968; (k) Cordova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, III, C. F. J. Am. Chem. Soc. 2002, 124, 1842-1843; (l) Cordova, A.; Watanabe, S.; Tanaka, F.; Notz, W.; Barbas, III, C. F. J. Am. Chem. Soc. 2002, 124, 1866-1867; (m) Markidis, T.; Kokotos, G. J. Org. Chem. 2002, 67, 1685-1688; (n) Collier, P. N.; Campbell, A. D.; Patel, I.; Raynham, T. M.; Taylor, R. J. K. J. Org. Chem. 2002, 67, 1802-1815; (o) Collier, P. N.; Campbell, A. D.; Patel, I.; Taylor, R. J. K. Tetrahedron 2002, 58, 6117-6125.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 1866-1867
    • Cordova, A.1    Watanabe, S.2    Tanaka, F.3    Notz, W.4    Barbas C.F. III5
  • 26
    • 0037040712 scopus 로고    scopus 로고
    • For selected recent publications, see: (a) Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445-446; (b) Kimura, T.; Vassilev, V. P.; Shen, G.-J.; Wong, C.-H. J. Am. Chem. Soc. 1997, 119, 11734-11742; (c) Kokotos, G.; Padrón, J. M.; Martín, T.; Gibbons, W. A.; Martín, V. S. J. Org. Chem. 1998, 63, 3741-3744; (d) Sibi, M. P.; Rutherford, D.; Renhowe, P. A.; Li, B. J. Am. Chem. Soc. 1999, 121, 7509-7516; (e) Ishitani, H.; Komiyama, S.; Hasegawa, Y.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 762-766; (f) Saaby, S.; Fang, X.; Gathergood, N.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2000, 39, 4114-4116; (g) Sabat, M.; Jonson, C. R. Org. Lett. 2000, 2, 1089-1092; (h) Collier, P. N.; Campbell, A. D.; Patel, I.; Taylor, R. J. K. Tetrahedron Lett. 2000, 41, 7115-7119; (i) Yao, S.; Saaby, S.; Hazell, R. G.; Jørgensen, K. A. Chem. Eur. J. 2000, 6, 2435-2448; (j) Atfani, M.; Wei, L.; Lubell, W. D. Org. Lett. 2001, 3, 2965-2968; (k) Cordova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, III, C. F. J. Am. Chem. Soc. 2002, 124, 1842-1843; (l) Cordova, A.; Watanabe, S.; Tanaka, F.; Notz, W.; Barbas, III, C. F. J. Am. Chem. Soc. 2002, 124, 1866-1867; (m) Markidis, T.; Kokotos, G. J. Org. Chem. 2002, 67, 1685-1688; (n) Collier, P. N.; Campbell, A. D.; Patel, I.; Raynham, T. M.; Taylor, R. J. K. J. Org. Chem. 2002, 67, 1802-1815; (o) Collier, P. N.; Campbell, A. D.; Patel, I.; Taylor, R. J. K. Tetrahedron 2002, 58, 6117-6125.
    • (2002) J. Org. Chem. , vol.67 , pp. 1685-1688
    • Markidis, T.1    Kokotos, G.2
  • 27
    • 0037155505 scopus 로고    scopus 로고
    • For selected recent publications, see: (a) Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445-446; (b) Kimura, T.; Vassilev, V. P.; Shen, G.-J.; Wong, C.-H. J. Am. Chem. Soc. 1997, 119, 11734-11742; (c) Kokotos, G.; Padrón, J. M.; Martín, T.; Gibbons, W. A.; Martín, V. S. J. Org. Chem. 1998, 63, 3741-3744; (d) Sibi, M. P.; Rutherford, D.; Renhowe, P. A.; Li, B. J. Am. Chem. Soc. 1999, 121, 7509-7516; (e) Ishitani, H.; Komiyama, S.; Hasegawa, Y.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 762-766; (f) Saaby, S.; Fang, X.; Gathergood, N.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2000, 39, 4114-4116; (g) Sabat, M.; Jonson, C. R. Org. Lett. 2000, 2, 1089-1092; (h) Collier, P. N.; Campbell, A. D.; Patel, I.; Taylor, R. J. K. Tetrahedron Lett. 2000, 41, 7115-7119; (i) Yao, S.; Saaby, S.; Hazell, R. G.; Jørgensen, K. A. Chem. Eur. J. 2000, 6, 2435-2448; (j) Atfani, M.; Wei, L.; Lubell, W. D. Org. Lett. 2001, 3, 2965-2968; (k) Cordova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, III, C. F. J. Am. Chem. Soc. 2002, 124, 1842-1843; (l) Cordova, A.; Watanabe, S.; Tanaka, F.; Notz, W.; Barbas, III, C. F. J. Am. Chem. Soc. 2002, 124, 1866-1867; (m) Markidis, T.; Kokotos, G. J. Org. Chem. 2002, 67, 1685-1688; (n) Collier, P. N.; Campbell, A. D.; Patel, I.; Raynham, T. M.; Taylor, R. J. K. J. Org. Chem. 2002, 67, 1802-1815; (o) Collier, P. N.; Campbell, A. D.; Patel, I.; Taylor, R. J. K. Tetrahedron 2002, 58, 6117-6125.
    • (2002) J. Org. Chem. , vol.67 , pp. 1802-1815
    • Collier, P.N.1    Campbell, A.D.2    Patel, I.3    Raynham, T.M.4    Taylor, R.J.K.5
  • 28
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    • For selected recent publications, see: (a) Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445-446; (b) Kimura, T.; Vassilev, V. P.; Shen, G.-J.; Wong, C.-H. J. Am. Chem. Soc. 1997, 119, 11734-11742; (c) Kokotos, G.; Padrón, J. M.; Martín, T.; Gibbons, W. A.; Martín, V. S. J. Org. Chem. 1998, 63, 3741-3744; (d) Sibi, M. P.; Rutherford, D.; Renhowe, P. A.; Li, B. J. Am. Chem. Soc. 1999, 121, 7509-7516; (e) Ishitani, H.; Komiyama, S.; Hasegawa, Y.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 762-766; (f) Saaby, S.; Fang, X.; Gathergood, N.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2000, 39, 4114-4116; (g) Sabat, M.; Jonson, C. R. Org. Lett. 2000, 2, 1089-1092; (h) Collier, P. N.; Campbell, A. D.; Patel, I.; Taylor, R. J. K. Tetrahedron Lett. 2000, 41, 7115-7119; (i) Yao, S.; Saaby, S.; Hazell, R. G.; Jørgensen, K. A. Chem. Eur. J. 2000, 6, 2435-2448; (j) Atfani, M.; Wei, L.; Lubell, W. D. Org. Lett. 2001, 3, 2965-2968; (k) Cordova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, III, C. F. J. Am. Chem. Soc. 2002, 124, 1842-1843; (l) Cordova, A.; Watanabe, S.; Tanaka, F.; Notz, W.; Barbas, III, C. F. J. Am. Chem. Soc. 2002, 124, 1866-1867; (m) Markidis, T.; Kokotos, G. J. Org. Chem. 2002, 67, 1685-1688; (n) Collier, P. N.; Campbell, A. D.; Patel, I.; Raynham, T. M.; Taylor, R. J. K. J. Org. Chem. 2002, 67, 1802-1815; (o) Collier, P. N.; Campbell, A. D.; Patel, I.; Taylor, R. J. K. Tetrahedron 2002, 58, 6117-6125.
    • (2002) Tetrahedron , vol.58 , pp. 6117-6125
    • Collier, P.N.1    Campbell, A.D.2    Patel, I.3    Taylor, R.J.K.4
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    • All new compounds gave spectroscopic and analytical data consistent with the proposed structures. These data and detailed experimental procedures will be given in a full paper.
    • All new compounds gave spectroscopic and analytical data consistent with the proposed structures. These data and detailed experimental procedures will be given in a full paper.
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    • note
    • The absolute configuration of C-3 and/or C-6 stereocentres in compounds 30, 31 and 32 could not be determined at this point. It became feasible by converting 32 to D-proline 34 (Scheme 3).


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