Asymmetric formation of quaternary centers through aza-annulation of chiral β-enamino amides with acrylate derivatives

Journal of the American Chemical Society

Volumn 120, Issue 11, 1998, Pages 2493-2500

  Benovsky, Petr ^a   Stephenson, Gregory A ^b   Stille, John R ^b  

^a MICHIGAN STATE UNIVERSITY   (United States)

^b ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC ACID DERIVATIVE; AMIDE; CHLOROFORMIC ACID ETHYL ESTER; ENAMINE;

ARTICLE; CHIRALITY; CRYSTAL STRUCTURE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0032565066     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9729591     Document Type: Article

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32. For previous reports of the use of 2-amidoacrylic acid derivatives in aza-annulation, see: (a) Thyagarajan, B. S.; Gopalakrishnan, P. V. Tetrahedron 1964, 20, 1051. (b) Meyer, H.; Bossert, F.; Horstmann, H. Justus Liebigs Ann. Chem. 1978, 1483. (a) Danieli, B.; Lesma, G.; Palmisano, G. J. Chem. Soc., Chem. Commun. 1980, 109. (c) Danieli, B.; Lesma, G.; Palmisano, G. Gazz. Chim. Ital. 1981, 111, 257. (c) McCabe, R. W.; Young, D. W.; Davies, G. M J. Chem. Soc., Chem. Commun. 1981, 395. (d) Chiba, T.; Takahashi, T. Chem. Pharm. Bull. 1985, 33, 2731. (e) Chiba, T.; Takahashi, T.; Kaneko, C. Chem. Pharm. Bull. 1985, 33, 4002. (f) Capps, N. K.; Davies, G. M.; Loakes, D.; McCabe, R. W.; Young, D. W. J. Chem. Soc., Perkin Trans. 1 1991, 3077. (g) Hua, D. H.; Park, J.-G.; Katsuhira, T.; Bharathi, S. N. J. Org. Chem. 1993, 58, 2144. (h) Kolar, P.; Tisler, M. J. Heterocycl. Chem. 1993, 30, 1253.
33. For previous reports of the use of 2-amidoacrylic acid derivatives in aza-annulation, see: (a) Thyagarajan, B. S.; Gopalakrishnan, P. V. Tetrahedron 1964, 20, 1051. (b) Meyer, H.; Bossert, F.; Horstmann, H. Justus Liebigs Ann. Chem. 1978, 1483. (a) Danieli, B.; Lesma, G.; Palmisano, G. J. Chem. Soc., Chem. Commun. 1980, 109. (c) Danieli, B.; Lesma, G.; Palmisano, G. Gazz. Chim. Ital. 1981, 111, 257. (c) McCabe, R. W.; Young, D. W.; Davies, G. M J. Chem. Soc., Chem. Commun. 1981, 395. (d) Chiba, T.; Takahashi, T. Chem. Pharm. Bull. 1985, 33, 2731. (e) Chiba, T.; Takahashi, T.; Kaneko, C. Chem. Pharm. Bull. 1985, 33, 4002. (f) Capps, N. K.; Davies, G. M.; Loakes, D.; McCabe, R. W.; Young, D. W. J. Chem. Soc., Perkin Trans. 1 1991, 3077. (g) Hua, D. H.; Park, J.-G.; Katsuhira, T.; Bharathi, S. N. J. Org. Chem. 1993, 58, 2144. (h) Kolar, P.; Tisler, M. J. Heterocycl. Chem. 1993, 30, 1253.
34. For previous reports of the use of 2-amidoacrylic acid derivatives in aza-annulation, see: (a) Thyagarajan, B. S.; Gopalakrishnan, P. V. Tetrahedron 1964, 20, 1051. (b) Meyer, H.; Bossert, F.; Horstmann, H. Justus Liebigs Ann. Chem. 1978, 1483. (a) Danieli, B.; Lesma, G.; Palmisano, G. J. Chem. Soc., Chem. Commun. 1980, 109. (c) Danieli, B.; Lesma, G.; Palmisano, G. Gazz. Chim. Ital. 1981, 111, 257. (c) McCabe, R. W.; Young, D. W.; Davies, G. M J. Chem. Soc., Chem. Commun. 1981, 395. (d) Chiba, T.; Takahashi, T. Chem. Pharm. Bull. 1985, 33, 2731. (e) Chiba, T.; Takahashi, T.; Kaneko, C. Chem. Pharm. Bull. 1985, 33, 4002. (f) Capps, N. K.; Davies, G. M.; Loakes, D.; McCabe, R. W.; Young, D. W. J. Chem. Soc., Perkin Trans. 1 1991, 3077. (g) Hua, D. H.; Park, J.-G.; Katsuhira, T.; Bharathi, S. N. J. Org. Chem. 1993, 58, 2144. (h) Kolar, P.; Tisler, M. J. Heterocycl. Chem. 1993, 30, 1253.
35. For previous reports of the use of 2-amidoacrylic acid derivatives in aza-annulation, see: (a) Thyagarajan, B. S.; Gopalakrishnan, P. V. Tetrahedron 1964, 20, 1051. (b) Meyer, H.; Bossert, F.; Horstmann, H. Justus Liebigs Ann. Chem. 1978, 1483. (a) Danieli, B.; Lesma, G.; Palmisano, G. J. Chem. Soc., Chem. Commun. 1980, 109. (c) Danieli, B.; Lesma, G.; Palmisano, G. Gazz. Chim. Ital. 1981, 111, 257. (c) McCabe, R. W.; Young, D. W.; Davies, G. M J. Chem. Soc., Chem. Commun. 1981, 395. (d) Chiba, T.; Takahashi, T. Chem. Pharm. Bull. 1985, 33, 2731. (e) Chiba, T.; Takahashi, T.; Kaneko, C. Chem. Pharm. Bull. 1985, 33, 4002. (f) Capps, N. K.; Davies, G. M.; Loakes, D.; McCabe, R. W.; Young, D. W. J. Chem. Soc., Perkin Trans. 1 1991, 3077. (g) Hua, D. H.; Park, J.-G.; Katsuhira, T.; Bharathi, S. N. J. Org. Chem. 1993, 58, 2144. (h) Kolar, P.; Tisler, M. J. Heterocycl. Chem. 1993, 30, 1253.
36. For previous reports of the use of 2-amidoacrylic acid derivatives in aza-annulation, see: (a) Thyagarajan, B. S.; Gopalakrishnan, P. V. Tetrahedron 1964, 20, 1051. (b) Meyer, H.; Bossert, F.; Horstmann, H. Justus Liebigs Ann. Chem. 1978, 1483. (a) Danieli, B.; Lesma, G.; Palmisano, G. J. Chem. Soc., Chem. Commun. 1980, 109. (c) Danieli, B.; Lesma, G.; Palmisano, G. Gazz. Chim. Ital. 1981, 111, 257. (c) McCabe, R. W.; Young, D. W.; Davies, G. M J. Chem. Soc., Chem. Commun. 1981, 395. (d) Chiba, T.; Takahashi, T. Chem. Pharm. Bull. 1985, 33, 2731. (e) Chiba, T.; Takahashi, T.; Kaneko, C. Chem. Pharm. Bull. 1985, 33, 4002. (f) Capps, N. K.; Davies, G. M.; Loakes, D.; McCabe, R. W.; Young, D. W. J. Chem. Soc., Perkin Trans. 1 1991, 3077. (g) Hua, D. H.; Park, J.-G.; Katsuhira, T.; Bharathi, S. N. J. Org. Chem. 1993, 58, 2144. (h) Kolar, P.; Tisler, M. J. Heterocycl. Chem. 1993, 30, 1253.
37. For previous reports of the use of 2-amidoacrylic acid derivatives in aza-annulation, see: (a) Thyagarajan, B. S.; Gopalakrishnan, P. V. Tetrahedron 1964, 20, 1051. (b) Meyer, H.; Bossert, F.; Horstmann, H. Justus Liebigs Ann. Chem. 1978, 1483. (a) Danieli, B.; Lesma, G.; Palmisano, G. J. Chem. Soc., Chem. Commun. 1980, 109. (c) Danieli, B.; Lesma, G.; Palmisano, G. Gazz. Chim. Ital. 1981, 111, 257. (c) McCabe, R. W.; Young, D. W.; Davies, G. M J. Chem. Soc., Chem. Commun. 1981, 395. (d) Chiba, T.; Takahashi, T. Chem. Pharm. Bull. 1985, 33, 2731. (e) Chiba, T.; Takahashi, T.; Kaneko, C. Chem. Pharm. Bull. 1985, 33, 4002. (f) Capps, N. K.; Davies, G. M.; Loakes, D.; McCabe, R. W.; Young, D. W. J. Chem. Soc., Perkin Trans. 1 1991, 3077. (g) Hua, D. H.; Park, J.-G.; Katsuhira, T.; Bharathi, S. N. J. Org. Chem. 1993, 58, 2144. (h) Kolar, P.; Tisler, M. J. Heterocycl. Chem. 1993, 30, 1253.
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