Chiral bicyclic lactams as homoenolate equivalents: An asymmetric route to 5-substituted cyclohexenones

Tetrahedron

Volumn 53, Issue 26, 1997, Pages 8795-8806

  Schwarz, Jacob B ^a   Devine, Paul N ^a   Meyers, A I ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 CYCLOHEXENONE; ALPHA CYANOENAMINE; LACTAM; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; DIAGNOSTIC APPROACH ROUTE; ENANTIOMER; HYDROLYSIS; PRIORITY JOURNAL; STEREOCHEMISTRY; STEREOISOMERISM; STRUCTURE ANALYSIS;

EID: 0030854055     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)90391-4     Document Type: Article

References (37)

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23. For some approaches to chiral 5-substituted cyclohexenones, see: (a) Asaoka, M.; Shima, K.; Takei, H. Tetrahedron Lett. 1987, 28, 5669. (b) Liu, H.-J.; Ralitsch, M. J. Chem. Soc. Chem. Comm. 1990, 997. (c) Kuwahara, S.; Mori, K. Tetrahedron 1990, 46, 8075. (d) Chapuis, C.; Winter, B.; Schulte-Elte, K. H. Tetrahedron Lett. 1992, 33, 6135. (e) Chapuis, C.; Brauchli, R. Helv. Chim. Acta. 1992, 75, 1527. (f) Chapuis, C.; Brauchli, R.; Thommen, W. Helv. Chim. Acta. 1993, 76, 535. (g) Takano, S.; Higashi, Y.; Kamikubo, T.; Moriya, M.; Ogasawara, K. J. Chem. Soc. Chem. Comm.1993, 788. (h) Takano, S.; Moriya, M.; Ogasawara, K. Synlett, 1993, 601. (i) Miyaoka, H.; Sagawa, S.; Inoue, T.; Nagaoka, H.; Yamada, Y. Chem. Pharm. Bull. 1994, 42, 405. (j) Wada, E.; Yasuoka, H.; Kanemasa, S. Chem. Lett. 1994, 1637. (k) Pearson, A. J.; Gontcharov, A. V.; Woodgate, P. D. Tetrahedron Lett. 1996, 37, 3087. (l) Semmelhack, M. F.; Schmalz, H.-G. Tetrahedron Lett. 1996, 37, 3089.
24. For some approaches to chiral 5-substituted cyclohexenones, see: (a) Asaoka, M.; Shima, K.; Takei, H. Tetrahedron Lett. 1987, 28, 5669. (b) Liu, H.-J.; Ralitsch, M. J. Chem. Soc. Chem. Comm. 1990, 997. (c) Kuwahara, S.; Mori, K. Tetrahedron 1990, 46, 8075. (d) Chapuis, C.; Winter, B.; Schulte-Elte, K. H. Tetrahedron Lett. 1992, 33, 6135. (e) Chapuis, C.; Brauchli, R. Helv. Chim. Acta. 1992, 75, 1527. (f) Chapuis, C.; Brauchli, R.; Thommen, W. Helv. Chim. Acta. 1993, 76, 535. (g) Takano, S.; Higashi, Y.; Kamikubo, T.; Moriya, M.; Ogasawara, K. J. Chem. Soc. Chem. Comm.1993, 788. (h) Takano, S.; Moriya, M.; Ogasawara, K. Synlett, 1993, 601. (i) Miyaoka, H.; Sagawa, S.; Inoue, T.; Nagaoka, H.; Yamada, Y. Chem. Pharm. Bull. 1994, 42, 405. (j) Wada, E.; Yasuoka, H.; Kanemasa, S. Chem. Lett. 1994, 1637. (k) Pearson, A. J.; Gontcharov, A. V.; Woodgate, P. D. Tetrahedron Lett. 1996, 37, 3087. (l) Semmelhack, M. F.; Schmalz, H.-G. Tetrahedron Lett. 1996, 37, 3089.
25. For some approaches to chiral 5-substituted cyclohexenones, see: (a) Asaoka, M.; Shima, K.; Takei, H. Tetrahedron Lett. 1987, 28, 5669. (b) Liu, H.-J.; Ralitsch, M. J. Chem. Soc. Chem. Comm. 1990, 997. (c) Kuwahara, S.; Mori, K. Tetrahedron 1990, 46, 8075. (d) Chapuis, C.; Winter, B.; Schulte-Elte, K. H. Tetrahedron Lett. 1992, 33, 6135. (e) Chapuis, C.; Brauchli, R. Helv. Chim. Acta. 1992, 75, 1527. (f) Chapuis, C.; Brauchli, R.; Thommen, W. Helv. Chim. Acta. 1993, 76, 535. (g) Takano, S.; Higashi, Y.; Kamikubo, T.; Moriya, M.; Ogasawara, K. J. Chem. Soc. Chem. Comm.1993, 788. (h) Takano, S.; Moriya, M.; Ogasawara, K. Synlett, 1993, 601. (i) Miyaoka, H.; Sagawa, S.; Inoue, T.; Nagaoka, H.; Yamada, Y. Chem. Pharm. Bull. 1994, 42, 405. (j) Wada, E.; Yasuoka, H.; Kanemasa, S. Chem. Lett. 1994, 1637. (k) Pearson, A. J.; Gontcharov, A. V.; Woodgate, P. D. Tetrahedron Lett. 1996, 37, 3087. (l) Semmelhack, M. F.; Schmalz, H.-G. Tetrahedron Lett. 1996, 37, 3089.
26. For some approaches to chiral 5-substituted cyclohexenones, see: (a) Asaoka, M.; Shima, K.; Takei, H. Tetrahedron Lett. 1987, 28, 5669. (b) Liu, H.-J.; Ralitsch, M. J. Chem. Soc. Chem. Comm. 1990, 997. (c) Kuwahara, S.; Mori, K. Tetrahedron 1990, 46, 8075. (d) Chapuis, C.; Winter, B.; Schulte-Elte, K. H. Tetrahedron Lett. 1992, 33, 6135. (e) Chapuis, C.; Brauchli, R. Helv. Chim. Acta. 1992, 75, 1527. (f) Chapuis, C.; Brauchli, R.; Thommen, W. Helv. Chim. Acta. 1993, 76, 535. (g) Takano, S.; Higashi, Y.; Kamikubo, T.; Moriya, M.; Ogasawara, K. J. Chem. Soc. Chem. Comm.1993, 788. (h) Takano, S.; Moriya, M.; Ogasawara, K. Synlett, 1993, 601. (i) Miyaoka, H.; Sagawa, S.; Inoue, T.; Nagaoka, H.; Yamada, Y. Chem. Pharm. Bull. 1994, 42, 405. (j) Wada, E.; Yasuoka, H.; Kanemasa, S. Chem. Lett. 1994, 1637. (k) Pearson, A. J.; Gontcharov, A. V.; Woodgate, P. D. Tetrahedron Lett. 1996, 37, 3087. (l) Semmelhack, M. F.; Schmalz, H.-G. Tetrahedron Lett. 1996, 37, 3089.
27. For some approaches to chiral 5-substituted cyclohexenones, see: (a) Asaoka, M.; Shima, K.; Takei, H. Tetrahedron Lett. 1987, 28, 5669. (b) Liu, H.-J.; Ralitsch, M. J. Chem. Soc. Chem. Comm. 1990, 997. (c) Kuwahara, S.; Mori, K. Tetrahedron 1990, 46, 8075. (d) Chapuis, C.; Winter, B.; Schulte-Elte, K. H. Tetrahedron Lett. 1992, 33, 6135. (e) Chapuis, C.; Brauchli, R. Helv. Chim. Acta. 1992, 75, 1527. (f) Chapuis, C.; Brauchli, R.; Thommen, W. Helv. Chim. Acta. 1993, 76, 535. (g) Takano, S.; Higashi, Y.; Kamikubo, T.; Moriya, M.; Ogasawara, K. J. Chem. Soc. Chem. Comm.1993, 788. (h) Takano, S.; Moriya, M.; Ogasawara, K. Synlett, 1993, 601. (i) Miyaoka, H.; Sagawa, S.; Inoue, T.; Nagaoka, H.; Yamada, Y. Chem. Pharm. Bull. 1994, 42, 405. (j) Wada, E.; Yasuoka, H.; Kanemasa, S. Chem. Lett. 1994, 1637. (k) Pearson, A. J.; Gontcharov, A. V.; Woodgate, P. D. Tetrahedron Lett. 1996, 37, 3087. (l) Semmelhack, M. F.; Schmalz, H.-G. Tetrahedron Lett. 1996, 37, 3089.
28. For some approaches to chiral 5-substituted cyclohexenones, see: (a) Asaoka, M.; Shima, K.; Takei, H. Tetrahedron Lett. 1987, 28, 5669. (b) Liu, H.-J.; Ralitsch, M. J. Chem. Soc. Chem. Comm. 1990, 997. (c) Kuwahara, S.; Mori, K. Tetrahedron 1990, 46, 8075. (d) Chapuis, C.; Winter, B.; Schulte-Elte, K. H. Tetrahedron Lett. 1992, 33, 6135. (e) Chapuis, C.; Brauchli, R. Helv. Chim. Acta. 1992, 75, 1527. (f) Chapuis, C.; Brauchli, R.; Thommen, W. Helv. Chim. Acta. 1993, 76, 535. (g) Takano, S.; Higashi, Y.; Kamikubo, T.; Moriya, M.; Ogasawara, K. J. Chem. Soc. Chem. Comm.1993, 788. (h) Takano, S.; Moriya, M.; Ogasawara, K. Synlett, 1993, 601. (i) Miyaoka, H.; Sagawa, S.; Inoue, T.; Nagaoka, H.; Yamada, Y. Chem. Pharm. Bull. 1994, 42, 405. (j) Wada, E.; Yasuoka, H.; Kanemasa, S. Chem. Lett. 1994, 1637. (k) Pearson, A. J.; Gontcharov, A. V.; Woodgate, P. D. Tetrahedron Lett. 1996, 37, 3087. (l) Semmelhack, M. F.; Schmalz, H.-G. Tetrahedron Lett. 1996, 37, 3089.
29. For some approaches to chiral 5-substituted cyclohexenones, see: (a) Asaoka, M.; Shima, K.; Takei, H. Tetrahedron Lett. 1987, 28, 5669. (b) Liu, H.-J.; Ralitsch, M. J. Chem. Soc. Chem. Comm. 1990, 997. (c) Kuwahara, S.; Mori, K. Tetrahedron 1990, 46, 8075. (d) Chapuis, C.; Winter, B.; Schulte-Elte, K. H. Tetrahedron Lett. 1992, 33, 6135. (e) Chapuis, C.; Brauchli, R. Helv. Chim. Acta. 1992, 75, 1527. (f) Chapuis, C.; Brauchli, R.; Thommen, W. Helv. Chim. Acta. 1993, 76, 535. (g) Takano, S.; Higashi, Y.; Kamikubo, T.; Moriya, M.; Ogasawara, K. J. Chem. Soc. Chem. Comm.1993, 788. (h) Takano, S.; Moriya, M.; Ogasawara, K. Synlett, 1993, 601. (i) Miyaoka, H.; Sagawa, S.; Inoue, T.; Nagaoka, H.; Yamada, Y. Chem. Pharm. Bull. 1994, 42, 405. (j) Wada, E.; Yasuoka, H.; Kanemasa, S. Chem. Lett. 1994, 1637. (k) Pearson, A. J.; Gontcharov, A. V.; Woodgate, P. D. Tetrahedron Lett. 1996, 37, 3087. (l) Semmelhack, M. F.; Schmalz, H.-G. Tetrahedron Lett. 1996, 37, 3089.
30. For some approaches to chiral 5-substituted cyclohexenones, see: (a) Asaoka, M.; Shima, K.; Takei, H. Tetrahedron Lett. 1987, 28, 5669. (b) Liu, H.-J.; Ralitsch, M. J. Chem. Soc. Chem. Comm. 1990, 997. (c) Kuwahara, S.; Mori, K. Tetrahedron 1990, 46, 8075. (d) Chapuis, C.; Winter, B.; Schulte-Elte, K. H. Tetrahedron Lett. 1992, 33, 6135. (e) Chapuis, C.; Brauchli, R. Helv. Chim. Acta. 1992, 75, 1527. (f) Chapuis, C.; Brauchli, R.; Thommen, W. Helv. Chim. Acta. 1993, 76, 535. (g) Takano, S.; Higashi, Y.; Kamikubo, T.; Moriya, M.; Ogasawara, K. J. Chem. Soc. Chem. Comm.1993, 788. (h) Takano, S.; Moriya, M.; Ogasawara, K. Synlett, 1993, 601. (i) Miyaoka, H.; Sagawa, S.; Inoue, T.; Nagaoka, H.; Yamada, Y. Chem. Pharm. Bull. 1994, 42, 405. (j) Wada, E.; Yasuoka, H.; Kanemasa, S. Chem. Lett. 1994, 1637. (k) Pearson, A. J.; Gontcharov, A. V.; Woodgate, P. D. Tetrahedron Lett. 1996, 37, 3087. (l) Semmelhack, M. F.; Schmalz, H.-G. Tetrahedron Lett. 1996, 37, 3089.
31. For some approaches to chiral 5-substituted cyclohexenones, see: (a) Asaoka, M.; Shima, K.; Takei, H. Tetrahedron Lett. 1987, 28, 5669. (b) Liu, H.-J.; Ralitsch, M. J. Chem. Soc. Chem. Comm. 1990, 997. (c) Kuwahara, S.; Mori, K. Tetrahedron 1990, 46, 8075. (d) Chapuis, C.; Winter, B.; Schulte-Elte, K. H. Tetrahedron Lett. 1992, 33, 6135. (e) Chapuis, C.; Brauchli, R. Helv. Chim. Acta. 1992, 75, 1527. (f) Chapuis, C.; Brauchli, R.; Thommen, W. Helv. Chim. Acta. 1993, 76, 535. (g) Takano, S.; Higashi, Y.; Kamikubo, T.; Moriya, M.; Ogasawara, K. J. Chem. Soc. Chem. Comm.1993, 788. (h) Takano, S.; Moriya, M.; Ogasawara, K. Synlett, 1993, 601. (i) Miyaoka, H.; Sagawa, S.; Inoue, T.; Nagaoka, H.; Yamada, Y. Chem. Pharm. Bull. 1994, 42, 405. (j) Wada, E.; Yasuoka, H.; Kanemasa, S. Chem. Lett. 1994, 1637. (k) Pearson, A. J.; Gontcharov, A. V.; Woodgate, P. D. Tetrahedron Lett. 1996, 37, 3087. (l) Semmelhack, M. F.; Schmalz, H.-G. Tetrahedron Lett. 1996, 37, 3089.
32. For some approaches to chiral 5-substituted cyclohexenones, see: (a) Asaoka, M.; Shima, K.; Takei, H. Tetrahedron Lett. 1987, 28, 5669. (b) Liu, H.-J.; Ralitsch, M. J. Chem. Soc. Chem. Comm. 1990, 997. (c) Kuwahara, S.; Mori, K. Tetrahedron 1990, 46, 8075. (d) Chapuis, C.; Winter, B.; Schulte-Elte, K. H. Tetrahedron Lett. 1992, 33, 6135. (e) Chapuis, C.; Brauchli, R. Helv. Chim. Acta. 1992, 75, 1527. (f) Chapuis, C.; Brauchli, R.; Thommen, W. Helv. Chim. Acta. 1993, 76, 535. (g) Takano, S.; Higashi, Y.; Kamikubo, T.; Moriya, M.; Ogasawara, K. J. Chem. Soc. Chem. Comm.1993, 788. (h) Takano, S.; Moriya, M.; Ogasawara, K. Synlett, 1993, 601. (i) Miyaoka, H.; Sagawa, S.; Inoue, T.; Nagaoka, H.; Yamada, Y. Chem. Pharm. Bull. 1994, 42, 405. (j) Wada, E.; Yasuoka, H.; Kanemasa, S. Chem. Lett. 1994, 1637. (k) Pearson, A. J.; Gontcharov, A. V.; Woodgate, P. D. Tetrahedron Lett. 1996, 37, 3087. (l) Semmelhack, M. F.; Schmalz, H.-G. Tetrahedron Lett. 1996, 37, 3089.
33. For some approaches to chiral 5-substituted cyclohexenones, see: (a) Asaoka, M.; Shima, K.; Takei, H. Tetrahedron Lett. 1987, 28, 5669. (b) Liu, H.-J.; Ralitsch, M. J. Chem. Soc. Chem. Comm. 1990, 997. (c) Kuwahara, S.; Mori, K. Tetrahedron 1990, 46, 8075. (d) Chapuis, C.; Winter, B.; Schulte-Elte, K. H. Tetrahedron Lett. 1992, 33, 6135. (e) Chapuis, C.; Brauchli, R. Helv. Chim. Acta. 1992, 75, 1527. (f) Chapuis, C.; Brauchli, R.; Thommen, W. Helv. Chim. Acta. 1993, 76, 535. (g) Takano, S.; Higashi, Y.; Kamikubo, T.; Moriya, M.; Ogasawara, K. J. Chem. Soc. Chem. Comm.1993, 788. (h) Takano, S.; Moriya, M.; Ogasawara, K. Synlett, 1993, 601. (i) Miyaoka, H.; Sagawa, S.; Inoue, T.; Nagaoka, H.; Yamada, Y. Chem. Pharm. Bull. 1994, 42, 405. (j) Wada, E.; Yasuoka, H.; Kanemasa, S. Chem. Lett. 1994, 1637. (k) Pearson, A. J.; Gontcharov, A. V.; Woodgate, P. D. Tetrahedron Lett. 1996, 37, 3087. (l) Semmelhack, M. F.; Schmalz, H.-G. Tetrahedron Lett. 1996, 37, 3089.
34. Oppolzer, W.; Petrzilka, M. Helv. Chim. Acta. 1978, 61, 2755.
35. Meyers, A. I.; Berney, D. Organic Synthesis 1990, 69, 55.
36. The procedure used herein was a modification of that previously described: Rossiter, B. E.; Eguchi, M.; Miao, G.; Swingle, N. M.; Hemandez, A. E.; Vickers, D.; Fluckiger, E.; Patterson, R. G.; Reddy, K. V. Tetrahedron 1993, 49, 965.
37. Prepared by the method previously described: Mitra, R. B.; Joshi, V. S. Synth. Comm. 1988, 18, 2259.