Asymmetric additions of alkyllithium to chiral imines - α- naphthylethyl group as a chiral auxiliary -

Chemical and Pharmaceutical Bulletin

Volumn 44, Issue 9, 1996, Pages 1776-1778

  Kawate, Tomohiko ^a   Yamada, Hideki ^a   Yamaguchi, Kentaro ^a   Nishida, Atsushi ^a   Nakagawa, Masako ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

asymmetric alkylation; chiral auxiliary; imine; optically active amines; naphthylethylamine

Indexed keywords

ALPHA NAPHTHYLETHYLAMINE; IMINE; LITHIUM DERIVATIVE; ORGANOMETALLIC COMPOUND; UNCLASSIFIED DRUG;

ALKYLATION; AMINE TRANSPORT; ARTICLE; BINDING KINETICS; CHIRALITY; DRUG BINDING; DRUG CONFORMATION; METHYLATION; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0029801352     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.44.1776     Document Type: Article

References (26)

1. Diastereoselective reactions: (a) H. Takahashi and Y. Suzuki, Chem. Pharm. Bull., 31, 4295-4299 (1983) (b) Y. Yamamoto, S. Nishii, K. Maruyama, T. Komatsu, and W. Ito, J. Am. Chem. Soc., 108, 7778-7786 (1986) (c) D. Enders, H. Shubert, and C. Nübling, Angew. Chem. Int. Ed. Engl., 25, 1109-1110 (1986) (d) C. Boga, D. Savoia, and A. Umani-Ronchi, Tetrahedron: Asymmetry, 1, 291-294 (1990) (e) S. Laschat and H. Kunz, J. Org. Chem., 56, 5883-5889 (1991) (f) Y. Ukaji, T. Watai, T. Sumi, and T. Fujisawa, Chem. Lett., 1991, 1555-1558 (g) S. E. Denmark, J. P. Edwards, and O. Nicaise, J. Org. Chem., 58, 569-578 (1993) (h) T. -K. Yang, R. -Y. Chen, D. -S. Lee, W. -S. Peng, Y. -Z. Jiang, A. -Q. Mi, and T. -T. Jong, J. Org. Chem., 59, 914-921 (1994) (i) H. Suzuki, S. Aoyagi, and C. Kibayashi, Tetrahedron Lett., 36, 6709-6712 (1995) (j) D. S. Brown, P.T. Gallagher, A. P. Lightfoot, C. J. Moody, A. M. Z. Slawin, and E. Swann, Tetrahedron, 51, 11473-11488 (1995) (k) K. Higashiyama, H. Fujikura, and H. Takahashi, Chem. Pharm. Bull., 43, 722-728 (1995) Enantioselective reactions: (l) K. Tomioka, M. Shindo, and K. Koga, J. Am. Chem. Soc., 111, 8266-8268 (1989) (m) K. Tomioka, I. Inoue, M. Shindo, and K. Koga, Tetrahedron Lett., 31, 6681-6684 (1990) (n) K. Tomioka, I. Inoue, M. Shindo, and K. Koga, Tetrahedron Lett., 32, 3095-3098 (1991) (o) S. Itsuno, H. Yanaka, C. Hachisuka, and K. Ito, J. Chem. Soc., Perkin Trans. 1, 1991, 1341-1342 (p) K. Soai, T. Hatanaka, and T. Miyazawa, J. Chem. Soc., Chem. Commun., 1992, 1097-1098 (q) I. Inoue, M. Shindo, K. Koga, and K. Tomioka, Tetrahedron: Asymmetry, 4, 1603-1606 (1993) (r) I. Inoue, M. Shindo, K. Koga, and K. Tomioka, Tetrahedron, 50, 4429-4438 (1994) (s) S. E. Denmark, N. Nakajima, and O. J.-C. Nicaise, J. Am. Chem. Soc., 116, 8797-8798 (1994) (t) I. Inoue, M. Shindo, K. Koga, M. Kanai, and K. Tomioka, Tetrahedron: Asymmetry, 6, 2527-2533 (1995) Intramolecular reactions: (u) H. Waldmann, G. Schmidt, H. Henke, and M. Burkard, Angew. Chem. Int. Ed. Engl., 34, 2402-2403 (1995).
2. Diastereoselective reactions: (a) H. Takahashi and Y. Suzuki, Chem. Pharm. Bull., 31, 4295-4299 (1983) (b) Y. Yamamoto, S. Nishii, K. Maruyama, T. Komatsu, and W. Ito, J. Am. Chem. Soc., 108, 7778-7786 (1986) (c) D. Enders, H. Shubert, and C. Nübling, Angew. Chem. Int. Ed. Engl., 25, 1109-1110 (1986) (d) C. Boga, D. Savoia, and A. Umani-Ronchi, Tetrahedron: Asymmetry, 1, 291-294 (1990) (e) S. Laschat and H. Kunz, J. Org. Chem., 56, 5883-5889 (1991) (f) Y. Ukaji, T. Watai, T. Sumi, and T. Fujisawa, Chem. Lett., 1991, 1555-1558 (g) S. E. Denmark, J. P. Edwards, and O. Nicaise, J. Org. Chem., 58, 569-578 (1993) (h) T. -K. Yang, R. -Y. Chen, D. -S. Lee, W. -S. Peng, Y. -Z. Jiang, A. -Q. Mi, and T. -T. Jong, J. Org. Chem., 59, 914-921 (1994) (i) H. Suzuki, S. Aoyagi, and C. Kibayashi, Tetrahedron Lett., 36, 6709-6712 (1995) (j) D. S. Brown, P.T. Gallagher, A. P. Lightfoot, C. J. Moody, A. M. Z. Slawin, and E. Swann, Tetrahedron, 51, 11473-11488 (1995) (k) K. Higashiyama, H. Fujikura, and H. Takahashi, Chem. Pharm. Bull., 43, 722-728 (1995) Enantioselective reactions: (l) K. Tomioka, M. Shindo, and K. Koga, J. Am. Chem. Soc., 111, 8266-8268 (1989) (m) K. Tomioka, I. Inoue, M. Shindo, and K. Koga, Tetrahedron Lett., 31, 6681-6684 (1990) (n) K. Tomioka, I. Inoue, M. Shindo, and K. Koga, Tetrahedron Lett., 32, 3095-3098 (1991) (o) S. Itsuno, H. Yanaka, C. Hachisuka, and K. Ito, J. Chem. Soc., Perkin Trans. 1, 1991, 1341-1342 (p) K. Soai, T. Hatanaka, and T. Miyazawa, J. Chem. Soc., Chem. Commun., 1992, 1097-1098 (q) I. Inoue, M. Shindo, K. Koga, and K. Tomioka, Tetrahedron: Asymmetry, 4, 1603-1606 (1993) (r) I. Inoue, M. Shindo, K. Koga, and K. Tomioka, Tetrahedron, 50, 4429-4438 (1994) (s) S. E. Denmark, N. Nakajima, and O. J.-C. Nicaise, J. Am. Chem. Soc., 116, 8797-8798 (1994) (t) I. Inoue, M. Shindo, K. Koga, M. Kanai, and K. Tomioka, Tetrahedron: Asymmetry, 6, 2527-2533 (1995) Intramolecular reactions: (u) H. Waldmann, G. Schmidt, H. Henke, and M. Burkard, Angew. Chem. Int. Ed. Engl., 34, 2402-2403 (1995).
3. Diastereoselective reactions: (a) H. Takahashi and Y. Suzuki, Chem. Pharm. Bull., 31, 4295-4299 (1983) (b) Y. Yamamoto, S. Nishii, K. Maruyama, T. Komatsu, and W. Ito, J. Am. Chem. Soc., 108, 7778-7786 (1986) (c) D. Enders, H. Shubert, and C. Nübling, Angew. Chem. Int. Ed. Engl., 25, 1109-1110 (1986) (d) C. Boga, D. Savoia, and A. Umani-Ronchi, Tetrahedron: Asymmetry, 1, 291-294 (1990) (e) S. Laschat and H. Kunz, J. Org. Chem., 56, 5883-5889 (1991) (f) Y. Ukaji, T. Watai, T. Sumi, and T. Fujisawa, Chem. Lett., 1991, 1555-1558 (g) S. E. Denmark, J. P. Edwards, and O. Nicaise, J. Org. Chem., 58, 569-578 (1993) (h) T. -K. Yang, R. -Y. Chen, D. -S. Lee, W. -S. Peng, Y. -Z. Jiang, A. -Q. Mi, and T. -T. Jong, J. Org. Chem., 59, 914-921 (1994) (i) H. Suzuki, S. Aoyagi, and C. Kibayashi, Tetrahedron Lett., 36, 6709-6712 (1995) (j) D. S. Brown, P.T. Gallagher, A. P. Lightfoot, C. J. Moody, A. M. Z. Slawin, and E. Swann, Tetrahedron, 51, 11473-11488 (1995) (k) K. Higashiyama, H. Fujikura, and H. Takahashi, Chem. Pharm. Bull., 43, 722-728 (1995) Enantioselective reactions: (l) K. Tomioka, M. Shindo, and K. Koga, J. Am. Chem. Soc., 111, 8266-8268 (1989) (m) K. Tomioka, I. Inoue, M. Shindo, and K. Koga, Tetrahedron Lett., 31, 6681-6684 (1990) (n) K. Tomioka, I. Inoue, M. Shindo, and K. Koga, Tetrahedron Lett., 32, 3095-3098 (1991) (o) S. Itsuno, H. Yanaka, C. Hachisuka, and K. Ito, J. Chem. Soc., Perkin Trans. 1, 1991, 1341-1342 (p) K. Soai, T. Hatanaka, and T. Miyazawa, J. Chem. Soc., Chem. Commun., 1992, 1097-1098 (q) I. Inoue, M. Shindo, K. Koga, and K. Tomioka, Tetrahedron: Asymmetry, 4, 1603-1606 (1993) (r) I. Inoue, M. Shindo, K. Koga, and K. Tomioka, Tetrahedron, 50, 4429-4438 (1994) (s) S. E. Denmark, N. Nakajima, and O. J.-C. Nicaise, J. Am. Chem. Soc., 116, 8797-8798 (1994) (t) I. Inoue, M. Shindo, K. Koga, M. Kanai, and K. Tomioka, Tetrahedron: Asymmetry, 6, 2527-2533 (1995) Intramolecular reactions: (u) H. Waldmann, G. Schmidt, H. Henke, and M. Burkard, Angew. Chem. Int. Ed. Engl., 34, 2402-2403 (1995).
4. Diastereoselective reactions: (a) H. Takahashi and Y. Suzuki, Chem. Pharm. Bull., 31, 4295-4299 (1983) (b) Y. Yamamoto, S. Nishii, K. Maruyama, T. Komatsu, and W. Ito, J. Am. Chem. Soc., 108, 7778-7786 (1986) (c) D. Enders, H. Shubert, and C. Nübling, Angew. Chem. Int. Ed. Engl., 25, 1109-1110 (1986) (d) C. Boga, D. Savoia, and A. Umani-Ronchi, Tetrahedron: Asymmetry, 1, 291-294 (1990) (e) S. Laschat and H. Kunz, J. Org. Chem., 56, 5883-5889 (1991) (f) Y. Ukaji, T. Watai, T. Sumi, and T. Fujisawa, Chem. Lett., 1991, 1555-1558 (g) S. E. Denmark, J. P. Edwards, and O. Nicaise, J. Org. Chem., 58, 569-578 (1993) (h) T. -K. Yang, R. -Y. Chen, D. -S. Lee, W. -S. Peng, Y. -Z. Jiang, A. -Q. Mi, and T. -T. Jong, J. Org. Chem., 59, 914-921 (1994) (i) H. Suzuki, S. Aoyagi, and C. Kibayashi, Tetrahedron Lett., 36, 6709-6712 (1995) (j) D. S. Brown, P.T. Gallagher, A. P. Lightfoot, C. J. Moody, A. M. Z. Slawin, and E. Swann, Tetrahedron, 51, 11473-11488 (1995) (k) K. Higashiyama, H. Fujikura, and H. Takahashi, Chem. Pharm. Bull., 43, 722-728 (1995) Enantioselective reactions: (l) K. Tomioka, M. Shindo, and K. Koga, J. Am. Chem. Soc., 111, 8266-8268 (1989) (m) K. Tomioka, I. Inoue, M. Shindo, and K. Koga, Tetrahedron Lett., 31, 6681-6684 (1990) (n) K. Tomioka, I. Inoue, M. Shindo, and K. Koga, Tetrahedron Lett., 32, 3095-3098 (1991) (o) S. Itsuno, H. Yanaka, C. Hachisuka, and K. Ito, J. Chem. Soc., Perkin Trans. 1, 1991, 1341-1342 (p) K. Soai, T. Hatanaka, and T. Miyazawa, J. Chem. Soc., Chem. Commun., 1992, 1097-1098 (q) I. Inoue, M. Shindo, K. Koga, and K. Tomioka, Tetrahedron: Asymmetry, 4, 1603-1606 (1993) (r) I. Inoue, M. Shindo, K. Koga, and K. Tomioka, Tetrahedron, 50, 4429-4438 (1994) (s) S. E. Denmark, N. Nakajima, and O. J.-C. Nicaise, J. Am. Chem. Soc., 116, 8797-8798 (1994) (t) I. Inoue, M. Shindo, K. Koga, M. Kanai, and K. Tomioka, Tetrahedron: Asymmetry, 6, 2527-2533 (1995) Intramolecular reactions: (u) H. Waldmann, G. Schmidt, H. Henke, and M. Burkard, Angew. Chem. Int. Ed. Engl., 34, 2402-2403 (1995).
5. Diastereoselective reactions: (a) H. Takahashi and Y. Suzuki, Chem. Pharm. Bull., 31, 4295-4299 (1983) (b) Y. Yamamoto, S. Nishii, K. Maruyama, T. Komatsu, and W. Ito, J. Am. Chem. Soc., 108, 7778-7786 (1986) (c) D. Enders, H. Shubert, and C. Nübling, Angew. Chem. Int. Ed. Engl., 25, 1109-1110 (1986) (d) C. Boga, D. Savoia, and A. Umani-Ronchi, Tetrahedron: Asymmetry, 1, 291-294 (1990) (e) S. Laschat and H. Kunz, J. Org. Chem., 56, 5883-5889 (1991) (f) Y. Ukaji, T. Watai, T. Sumi, and T. Fujisawa, Chem. Lett., 1991, 1555-1558 (g) S. E. Denmark, J. P. Edwards, and O. Nicaise, J. Org. Chem., 58, 569-578 (1993) (h) T. -K. Yang, R. -Y. Chen, D. -S. Lee, W. -S. Peng, Y. -Z. Jiang, A. -Q. Mi, and T. -T. Jong, J. Org. Chem., 59, 914-921 (1994) (i) H. Suzuki, S. Aoyagi, and C. Kibayashi, Tetrahedron Lett., 36, 6709-6712 (1995) (j) D. S. Brown, P.T. Gallagher, A. P. Lightfoot, C. J. Moody, A. M. Z. Slawin, and E. Swann, Tetrahedron, 51, 11473-11488 (1995) (k) K. Higashiyama, H. Fujikura, and H. Takahashi, Chem. Pharm. Bull., 43, 722-728 (1995) Enantioselective reactions: (l) K. Tomioka, M. Shindo, and K. Koga, J. Am. Chem. Soc., 111, 8266-8268 (1989) (m) K. Tomioka, I. Inoue, M. Shindo, and K. Koga, Tetrahedron Lett., 31, 6681-6684 (1990) (n) K. Tomioka, I. Inoue, M. Shindo, and K. Koga, Tetrahedron Lett., 32, 3095-3098 (1991) (o) S. Itsuno, H. Yanaka, C. Hachisuka, and K. Ito, J. Chem. Soc., Perkin Trans. 1, 1991, 1341-1342 (p) K. Soai, T. Hatanaka, and T. Miyazawa, J. Chem. Soc., Chem. Commun., 1992, 1097-1098 (q) I. Inoue, M. Shindo, K. Koga, and K. Tomioka, Tetrahedron: Asymmetry, 4, 1603-1606 (1993) (r) I. Inoue, M. Shindo, K. Koga, and K. Tomioka, Tetrahedron, 50, 4429-4438 (1994) (s) S. E. Denmark, N. Nakajima, and O. J.-C. Nicaise, J. Am. Chem. Soc., 116, 8797-8798 (1994) (t) I. Inoue, M. Shindo, K. Koga, M. Kanai, and K. Tomioka, Tetrahedron: Asymmetry, 6, 2527-2533 (1995) Intramolecular reactions: (u) H. Waldmann, G. Schmidt, H. Henke, and M. Burkard, Angew. Chem. Int. Ed. Engl., 34, 2402-2403 (1995).
6. Diastereoselective reactions: (a) H. Takahashi and Y. Suzuki, Chem. Pharm. Bull., 31, 4295-4299 (1983) (b) Y. Yamamoto, S. Nishii, K. Maruyama, T. Komatsu, and W. Ito, J. Am. Chem. Soc., 108, 7778-7786 (1986) (c) D. Enders, H. Shubert, and C. Nübling, Angew. Chem. Int. Ed. Engl., 25, 1109-1110 (1986) (d) C. Boga, D. Savoia, and A. Umani-Ronchi, Tetrahedron: Asymmetry, 1, 291-294 (1990) (e) S. Laschat and H. Kunz, J. Org. Chem., 56, 5883-5889 (1991) (f) Y. Ukaji, T. Watai, T. Sumi, and T. Fujisawa, Chem. Lett., 1991, 1555-1558 (g) S. E. Denmark, J. P. Edwards, and O. Nicaise, J. Org. Chem., 58, 569-578 (1993) (h) T. -K. Yang, R. -Y. Chen, D. -S. Lee, W. -S. Peng, Y. -Z. Jiang, A. -Q. Mi, and T. -T. Jong, J. Org. Chem., 59, 914-921 (1994) (i) H. Suzuki, S. Aoyagi, and C. Kibayashi, Tetrahedron Lett., 36, 6709-6712 (1995) (j) D. S. Brown, P.T. Gallagher, A. P. Lightfoot, C. J. Moody, A. M. Z. Slawin, and E. Swann, Tetrahedron, 51, 11473-11488 (1995) (k) K. Higashiyama, H. Fujikura, and H. Takahashi, Chem. Pharm. Bull., 43, 722-728 (1995) Enantioselective reactions: (l) K. Tomioka, M. Shindo, and K. Koga, J. Am. Chem. Soc., 111, 8266-8268 (1989) (m) K. Tomioka, I. Inoue, M. Shindo, and K. Koga, Tetrahedron Lett., 31, 6681-6684 (1990) (n) K. Tomioka, I. Inoue, M. Shindo, and K. Koga, Tetrahedron Lett., 32, 3095-3098 (1991) (o) S. Itsuno, H. Yanaka, C. Hachisuka, and K. Ito, J. Chem. Soc., Perkin Trans. 1, 1991, 1341-1342 (p) K. Soai, T. Hatanaka, and T. Miyazawa, J. Chem. Soc., Chem. Commun., 1992, 1097-1098 (q) I. Inoue, M. Shindo, K. Koga, and K. Tomioka, Tetrahedron: Asymmetry, 4, 1603-1606 (1993) (r) I. Inoue, M. Shindo, K. Koga, and K. Tomioka, Tetrahedron, 50, 4429-4438 (1994) (s) S. E. Denmark, N. Nakajima, and O. J.-C. Nicaise, J. Am. Chem. Soc., 116, 8797-8798 (1994) (t) I. Inoue, M. Shindo, K. Koga, M. Kanai, and K. Tomioka, Tetrahedron: Asymmetry, 6, 2527-2533 (1995) Intramolecular reactions: (u) H. Waldmann, G. Schmidt, H. Henke, and M. Burkard, Angew. Chem. Int. Ed. Engl., 34, 2402-2403 (1995).
7. Diastereoselective reactions: (a) H. Takahashi and Y. Suzuki, Chem. Pharm. Bull., 31, 4295-4299 (1983) (b) Y. Yamamoto, S. Nishii, K. Maruyama, T. Komatsu, and W. Ito, J. Am. Chem. Soc., 108, 7778-7786 (1986) (c) D. Enders, H. Shubert, and C. Nübling, Angew. Chem. Int. Ed. Engl., 25, 1109-1110 (1986) (d) C. Boga, D. Savoia, and A. Umani-Ronchi, Tetrahedron: Asymmetry, 1, 291-294 (1990) (e) S. Laschat and H. Kunz, J. Org. Chem., 56, 5883-5889 (1991) (f) Y. Ukaji, T. Watai, T. Sumi, and T. Fujisawa, Chem. Lett., 1991, 1555-1558 (g) S. E. Denmark, J. P. Edwards, and O. Nicaise, J. Org. Chem., 58, 569-578 (1993) (h) T. -K. Yang, R. -Y. Chen, D. -S. Lee, W. -S. Peng, Y. -Z. Jiang, A. -Q. Mi, and T. -T. Jong, J. Org. Chem., 59, 914-921 (1994) (i) H. Suzuki, S. Aoyagi, and C. Kibayashi, Tetrahedron Lett., 36, 6709-6712 (1995) (j) D. S. Brown, P.T. Gallagher, A. P. Lightfoot, C. J. Moody, A. M. Z. Slawin, and E. Swann, Tetrahedron, 51, 11473-11488 (1995) (k) K. Higashiyama, H. Fujikura, and H. Takahashi, Chem. Pharm. Bull., 43, 722-728 (1995) Enantioselective reactions: (l) K. Tomioka, M. Shindo, and K. Koga, J. Am. Chem. Soc., 111, 8266-8268 (1989) (m) K. Tomioka, I. Inoue, M. Shindo, and K. Koga, Tetrahedron Lett., 31, 6681-6684 (1990) (n) K. Tomioka, I. Inoue, M. Shindo, and K. Koga, Tetrahedron Lett., 32, 3095-3098 (1991) (o) S. Itsuno, H. Yanaka, C. Hachisuka, and K. Ito, J. Chem. Soc., Perkin Trans. 1, 1991, 1341-1342 (p) K. Soai, T. Hatanaka, and T. Miyazawa, J. Chem. Soc., Chem. Commun., 1992, 1097-1098 (q) I. Inoue, M. Shindo, K. Koga, and K. Tomioka, Tetrahedron: Asymmetry, 4, 1603-1606 (1993) (r) I. Inoue, M. Shindo, K. Koga, and K. Tomioka, Tetrahedron, 50, 4429-4438 (1994) (s) S. E. Denmark, N. Nakajima, and O. J.-C. Nicaise, J. Am. Chem. Soc., 116, 8797-8798 (1994) (t) I. Inoue, M. Shindo, K. Koga, M. Kanai, and K. Tomioka, Tetrahedron: Asymmetry, 6, 2527-2533 (1995) Intramolecular reactions: (u) H. Waldmann, G. Schmidt, H. Henke, and M. Burkard, Angew. Chem. Int. Ed. Engl., 34, 2402-2403 (1995).
8. Diastereoselective reactions: (a) H. Takahashi and Y. Suzuki, Chem. Pharm. Bull., 31, 4295-4299 (1983) (b) Y. Yamamoto, S. Nishii, K. Maruyama, T. Komatsu, and W. Ito, J. Am. Chem. Soc., 108, 7778-7786 (1986) (c) D. Enders, H. Shubert, and C. Nübling, Angew. Chem. Int. Ed. Engl., 25, 1109-1110 (1986) (d) C. Boga, D. Savoia, and A. Umani-Ronchi, Tetrahedron: Asymmetry, 1, 291-294 (1990) (e) S. Laschat and H. Kunz, J. Org. Chem., 56, 5883-5889 (1991) (f) Y. Ukaji, T. Watai, T. Sumi, and T. Fujisawa, Chem. Lett., 1991, 1555-1558 (g) S. E. Denmark, J. P. Edwards, and O. Nicaise, J. Org. Chem., 58, 569-578 (1993) (h) T. -K. Yang, R. -Y. Chen, D. -S. Lee, W. -S. Peng, Y. -Z. Jiang, A. -Q. Mi, and T. -T. Jong, J. Org. Chem., 59, 914-921 (1994) (i) H. Suzuki, S. Aoyagi, and C. Kibayashi, Tetrahedron Lett., 36, 6709-6712 (1995) (j) D. S. Brown, P.T. Gallagher, A. P. Lightfoot, C. J. Moody, A. M. Z. Slawin, and E. Swann, Tetrahedron, 51, 11473-11488 (1995) (k) K. Higashiyama, H. Fujikura, and H. Takahashi, Chem. Pharm. Bull., 43, 722-728 (1995) Enantioselective reactions: (l) K. Tomioka, M. Shindo, and K. Koga, J. Am. Chem. Soc., 111, 8266-8268 (1989) (m) K. Tomioka, I. Inoue, M. Shindo, and K. Koga, Tetrahedron Lett., 31, 6681-6684 (1990) (n) K. Tomioka, I. Inoue, M. Shindo, and K. Koga, Tetrahedron Lett., 32, 3095-3098 (1991) (o) S. Itsuno, H. Yanaka, C. Hachisuka, and K. Ito, J. Chem. Soc., Perkin Trans. 1, 1991, 1341-1342 (p) K. Soai, T. Hatanaka, and T. Miyazawa, J. Chem. Soc., Chem. Commun., 1992, 1097-1098 (q) I. Inoue, M. Shindo, K. Koga, and K. Tomioka, Tetrahedron: Asymmetry, 4, 1603-1606 (1993) (r) I. Inoue, M. Shindo, K. Koga, and K. Tomioka, Tetrahedron, 50, 4429-4438 (1994) (s) S. E. Denmark, N. Nakajima, and O. J.-C. Nicaise, J. Am. Chem. Soc., 116, 8797-8798 (1994) (t) I. Inoue, M. Shindo, K. Koga, M. Kanai, and K. Tomioka, Tetrahedron: Asymmetry, 6, 2527-2533 (1995) Intramolecular reactions: (u) H. Waldmann, G. Schmidt, H. Henke, and M. Burkard, Angew. Chem. Int. Ed. Engl., 34, 2402-2403 (1995).
9. Diastereoselective reactions: (a) H. Takahashi and Y. Suzuki, Chem. Pharm. Bull., 31, 4295-4299 (1983) (b) Y. Yamamoto, S. Nishii, K. Maruyama, T. Komatsu, and W. Ito, J. Am. Chem. Soc., 108, 7778-7786 (1986) (c) D. Enders, H. Shubert, and C. Nübling, Angew. Chem. Int. Ed. Engl., 25, 1109-1110 (1986) (d) C. Boga, D. Savoia, and A. Umani-Ronchi, Tetrahedron: Asymmetry, 1, 291-294 (1990) (e) S. Laschat and H. Kunz, J. Org. Chem., 56, 5883-5889 (1991) (f) Y. Ukaji, T. Watai, T. Sumi, and T. Fujisawa, Chem. Lett., 1991, 1555-1558 (g) S. E. Denmark, J. P. Edwards, and O. Nicaise, J. Org. Chem., 58, 569-578 (1993) (h) T. -K. Yang, R. -Y. Chen, D. -S. Lee, W. -S. Peng, Y. -Z. Jiang, A. -Q. Mi, and T. -T. Jong, J. Org. Chem., 59, 914-921 (1994) (i) H. Suzuki, S. Aoyagi, and C. Kibayashi, Tetrahedron Lett., 36, 6709-6712 (1995) (j) D. S. Brown, P.T. Gallagher, A. P. Lightfoot, C. J. Moody, A. M. Z. Slawin, and E. Swann, Tetrahedron, 51, 11473-11488 (1995) (k) K. Higashiyama, H. Fujikura, and H. Takahashi, Chem. Pharm. Bull., 43, 722-728 (1995) Enantioselective reactions: (l) K. Tomioka, M. Shindo, and K. Koga, J. Am. Chem. Soc., 111, 8266-8268 (1989) (m) K. Tomioka, I. Inoue, M. Shindo, and K. Koga, Tetrahedron Lett., 31, 6681-6684 (1990) (n) K. Tomioka, I. Inoue, M. Shindo, and K. Koga, Tetrahedron Lett., 32, 3095-3098 (1991) (o) S. Itsuno, H. Yanaka, C. Hachisuka, and K. Ito, J. Chem. Soc., Perkin Trans. 1, 1991, 1341-1342 (p) K. Soai, T. Hatanaka, and T. Miyazawa, J. Chem. Soc., Chem. Commun., 1992, 1097-1098 (q) I. Inoue, M. Shindo, K. Koga, and K. Tomioka, Tetrahedron: Asymmetry, 4, 1603-1606 (1993) (r) I. Inoue, M. Shindo, K. Koga, and K. Tomioka, Tetrahedron, 50, 4429-4438 (1994) (s) S. E. Denmark, N. Nakajima, and O. J.-C. Nicaise, J. Am. Chem. Soc., 116, 8797-8798 (1994) (t) I. Inoue, M. Shindo, K. Koga, M. Kanai, and K. Tomioka, Tetrahedron: Asymmetry, 6, 2527-2533 (1995) Intramolecular reactions: (u) H. Waldmann, G. Schmidt, H. Henke, and M. Burkard, Angew. Chem. Int. Ed. Engl., 34, 2402-2403 (1995).
10. Diastereoselective reactions: (a) H. Takahashi and Y. Suzuki, Chem. Pharm. Bull., 31, 4295-4299 (1983) (b) Y. Yamamoto, S. Nishii, K. Maruyama, T. Komatsu, and W. Ito, J. Am. Chem. Soc., 108, 7778-7786 (1986) (c) D. Enders, H. Shubert, and C. Nübling, Angew. Chem. Int. Ed. Engl., 25, 1109-1110 (1986) (d) C. Boga, D. Savoia, and A. Umani-Ronchi, Tetrahedron: Asymmetry, 1, 291-294 (1990) (e) S. Laschat and H. Kunz, J. Org. Chem., 56, 5883-5889 (1991) (f) Y. Ukaji, T. Watai, T. Sumi, and T. Fujisawa, Chem. Lett., 1991, 1555-1558 (g) S. E. Denmark, J. P. Edwards, and O. Nicaise, J. Org. Chem., 58, 569-578 (1993) (h) T. -K. Yang, R. -Y. Chen, D. -S. Lee, W. -S. Peng, Y. -Z. Jiang, A. -Q. Mi, and T. -T. Jong, J. Org. Chem., 59, 914-921 (1994) (i) H. Suzuki, S. Aoyagi, and C. Kibayashi, Tetrahedron Lett., 36, 6709-6712 (1995) (j) D. S. Brown, P.T. Gallagher, A. P. Lightfoot, C. J. Moody, A. M. Z. Slawin, and E. Swann, Tetrahedron, 51, 11473-11488 (1995) (k) K. Higashiyama, H. Fujikura, and H. Takahashi, Chem. Pharm. Bull., 43, 722-728 (1995) Enantioselective reactions: (l) K. Tomioka, M. Shindo, and K. Koga, J. Am. Chem. Soc., 111, 8266-8268 (1989) (m) K. Tomioka, I. Inoue, M. Shindo, and K. Koga, Tetrahedron Lett., 31, 6681-6684 (1990) (n) K. Tomioka, I. Inoue, M. Shindo, and K. Koga, Tetrahedron Lett., 32, 3095-3098 (1991) (o) S. Itsuno, H. Yanaka, C. Hachisuka, and K. Ito, J. Chem. Soc., Perkin Trans. 1, 1991, 1341-1342 (p) K. Soai, T. Hatanaka, and T. Miyazawa, J. Chem. Soc., Chem. Commun., 1992, 1097-1098 (q) I. Inoue, M. Shindo, K. Koga, and K. Tomioka, Tetrahedron: Asymmetry, 4, 1603-1606 (1993) (r) I. Inoue, M. Shindo, K. Koga, and K. Tomioka, Tetrahedron, 50, 4429-4438 (1994) (s) S. E. Denmark, N. Nakajima, and O. J.-C. Nicaise, J. Am. Chem. Soc., 116, 8797-8798 (1994) (t) I. Inoue, M. Shindo, K. Koga, M. Kanai, and K. Tomioka, Tetrahedron: Asymmetry, 6, 2527-2533 (1995) Intramolecular reactions: (u) H. Waldmann, G. Schmidt, H. Henke, and M. Burkard, Angew. Chem. Int. Ed. Engl., 34, 2402-2403 (1995).
11. Diastereoselective reactions: (a) H. Takahashi and Y. Suzuki, Chem. Pharm. Bull., 31, 4295-4299 (1983) (b) Y. Yamamoto, S. Nishii, K. Maruyama, T. Komatsu, and W. Ito, J. Am. Chem. Soc., 108, 7778-7786 (1986) (c) D. Enders, H. Shubert, and C. Nübling, Angew. Chem. Int. Ed. Engl., 25, 1109-1110 (1986) (d) C. Boga, D. Savoia, and A. Umani-Ronchi, Tetrahedron: Asymmetry, 1, 291-294 (1990) (e) S. Laschat and H. Kunz, J. Org. Chem., 56, 5883-5889 (1991) (f) Y. Ukaji, T. Watai, T. Sumi, and T. Fujisawa, Chem. Lett., 1991, 1555-1558 (g) S. E. Denmark, J. P. Edwards, and O. Nicaise, J. Org. Chem., 58, 569-578 (1993) (h) T. -K. Yang, R. -Y. Chen, D. -S. Lee, W. -S. Peng, Y. -Z. Jiang, A. -Q. Mi, and T. -T. Jong, J. Org. Chem., 59, 914-921 (1994) (i) H. Suzuki, S. Aoyagi, and C. Kibayashi, Tetrahedron Lett., 36, 6709-6712 (1995) (j) D. S. Brown, P.T. Gallagher, A. P. Lightfoot, C. J. Moody, A. M. Z. Slawin, and E. Swann, Tetrahedron, 51, 11473-11488 (1995) (k) K. Higashiyama, H. Fujikura, and H. Takahashi, Chem. Pharm. Bull., 43, 722-728 (1995) Enantioselective reactions: (l) K. Tomioka, M. Shindo, and K. Koga, J. Am. Chem. Soc., 111, 8266-8268 (1989) (m) K. Tomioka, I. Inoue, M. Shindo, and K. Koga, Tetrahedron Lett., 31, 6681-6684 (1990) (n) K. Tomioka, I. Inoue, M. Shindo, and K. Koga, Tetrahedron Lett., 32, 3095-3098 (1991) (o) S. Itsuno, H. Yanaka, C. Hachisuka, and K. Ito, J. Chem. Soc., Perkin Trans. 1, 1991, 1341-1342 (p) K. Soai, T. Hatanaka, and T. Miyazawa, J. Chem. Soc., Chem. Commun., 1992, 1097-1098 (q) I. Inoue, M. Shindo, K. Koga, and K. Tomioka, Tetrahedron: Asymmetry, 4, 1603-1606 (1993) (r) I. Inoue, M. Shindo, K. Koga, and K. Tomioka, Tetrahedron, 50, 4429-4438 (1994) (s) S. E. Denmark, N. Nakajima, and O. J.-C. Nicaise, J. Am. Chem. Soc., 116, 8797-8798 (1994) (t) I. Inoue, M. Shindo, K. Koga, M. Kanai, and K. Tomioka, Tetrahedron: Asymmetry, 6, 2527-2533 (1995) Intramolecular reactions: (u) H. Waldmann, G. Schmidt, H. Henke, and M. Burkard, Angew. Chem. Int. Ed. Engl., 34, 2402-2403 (1995).
12. Diastereoselective reactions: (a) H. Takahashi and Y. Suzuki, Chem. Pharm. Bull., 31, 4295-4299 (1983) (b) Y. Yamamoto, S. Nishii, K. Maruyama, T. Komatsu, and W. Ito, J. Am. Chem. Soc., 108, 7778-7786 (1986) (c) D. Enders, H. Shubert, and C. Nübling, Angew. Chem. Int. Ed. Engl., 25, 1109-1110 (1986) (d) C. Boga, D. Savoia, and A. Umani-Ronchi, Tetrahedron: Asymmetry, 1, 291-294 (1990) (e) S. Laschat and H. Kunz, J. Org. Chem., 56, 5883-5889 (1991) (f) Y. Ukaji, T. Watai, T. Sumi, and T. Fujisawa, Chem. Lett., 1991, 1555-1558 (g) S. E. Denmark, J. P. Edwards, and O. Nicaise, J. Org. Chem., 58, 569-578 (1993) (h) T. -K. Yang, R. -Y. Chen, D. -S. Lee, W. -S. Peng, Y. -Z. Jiang, A. -Q. Mi, and T. -T. Jong, J. Org. Chem., 59, 914-921 (1994) (i) H. Suzuki, S. Aoyagi, and C. Kibayashi, Tetrahedron Lett., 36, 6709-6712 (1995) (j) D. S. Brown, P.T. Gallagher, A. P. Lightfoot, C. J. Moody, A. M. Z. Slawin, and E. Swann, Tetrahedron, 51, 11473-11488 (1995) (k) K. Higashiyama, H. Fujikura, and H. Takahashi, Chem. Pharm. Bull., 43, 722-728 (1995) Enantioselective reactions: (l) K. Tomioka, M. Shindo, and K. Koga, J. Am. Chem. Soc., 111, 8266-8268 (1989) (m) K. Tomioka, I. Inoue, M. Shindo, and K. Koga, Tetrahedron Lett., 31, 6681-6684 (1990) (n) K. Tomioka, I. Inoue, M. Shindo, and K. Koga, Tetrahedron Lett., 32, 3095-3098 (1991) (o) S. Itsuno, H. Yanaka, C. Hachisuka, and K. Ito, J. Chem. Soc., Perkin Trans. 1, 1991, 1341-1342 (p) K. Soai, T. Hatanaka, and T. Miyazawa, J. Chem. Soc., Chem. Commun., 1992, 1097-1098 (q) I. Inoue, M. Shindo, K. Koga, and K. Tomioka, Tetrahedron: Asymmetry, 4, 1603-1606 (1993) (r) I. Inoue, M. Shindo, K. Koga, and K. Tomioka, Tetrahedron, 50, 4429-4438 (1994) (s) S. E. Denmark, N. Nakajima, and O. J.-C. Nicaise, J. Am. Chem. Soc., 116, 8797-8798 (1994) (t) I. Inoue, M. Shindo, K. Koga, M. Kanai, and K. Tomioka, Tetrahedron: Asymmetry, 6, 2527-2533 (1995) Intramolecular reactions: (u) H. Waldmann, G. Schmidt, H. Henke, and M. Burkard, Angew. Chem. Int. Ed. Engl., 34, 2402-2403 (1995).
13. Diastereoselective reactions: (a) H. Takahashi and Y. Suzuki, Chem. Pharm. Bull., 31, 4295-4299 (1983) (b) Y. Yamamoto, S. Nishii, K. Maruyama, T. Komatsu, and W. Ito, J. Am. Chem. Soc., 108, 7778-7786 (1986) (c) D. Enders, H. Shubert, and C. Nübling, Angew. Chem. Int. Ed. Engl., 25, 1109-1110 (1986) (d) C. Boga, D. Savoia, and A. Umani-Ronchi, Tetrahedron: Asymmetry, 1, 291-294 (1990) (e) S. Laschat and H. Kunz, J. Org. Chem., 56, 5883-5889 (1991) (f) Y. Ukaji, T. Watai, T. Sumi, and T. Fujisawa, Chem. Lett., 1991, 1555-1558 (g) S. E. Denmark, J. P. Edwards, and O. Nicaise, J. Org. Chem., 58, 569-578 (1993) (h) T. -K. Yang, R. -Y. Chen, D. -S. Lee, W. -S. Peng, Y. -Z. Jiang, A. -Q. Mi, and T. -T. Jong, J. Org. Chem., 59, 914-921 (1994) (i) H. Suzuki, S. Aoyagi, and C. Kibayashi, Tetrahedron Lett., 36, 6709-6712 (1995) (j) D. S. Brown, P.T. Gallagher, A. P. Lightfoot, C. J. Moody, A. M. Z. Slawin, and E. Swann, Tetrahedron, 51, 11473-11488 (1995) (k) K. Higashiyama, H. Fujikura, and H. Takahashi, Chem. Pharm. Bull., 43, 722-728 (1995) Enantioselective reactions: (l) K. Tomioka, M. Shindo, and K. Koga, J. Am. Chem. Soc., 111, 8266-8268 (1989) (m) K. Tomioka, I. Inoue, M. Shindo, and K. Koga, Tetrahedron Lett., 31, 6681-6684 (1990) (n) K. Tomioka, I. Inoue, M. Shindo, and K. Koga, Tetrahedron Lett., 32, 3095-3098 (1991) (o) S. Itsuno, H. Yanaka, C. Hachisuka, and K. Ito, J. Chem. Soc., Perkin Trans. 1, 1991, 1341-1342 (p) K. Soai, T. Hatanaka, and T. Miyazawa, J. Chem. Soc., Chem. Commun., 1992, 1097-1098 (q) I. Inoue, M. Shindo, K. Koga, and K. Tomioka, Tetrahedron: Asymmetry, 4, 1603-1606 (1993) (r) I. Inoue, M. Shindo, K. Koga, and K. Tomioka, Tetrahedron, 50, 4429-4438 (1994) (s) S. E. Denmark, N. Nakajima, and O. J.-C. Nicaise, J. Am. Chem. Soc., 116, 8797-8798 (1994) (t) I. Inoue, M. Shindo, K. Koga, M. Kanai, and K. Tomioka, Tetrahedron: Asymmetry, 6, 2527-2533 (1995) Intramolecular reactions: (u) H. Waldmann, G. Schmidt, H. Henke, and M. Burkard, Angew. Chem. Int. Ed. Engl., 34, 2402-2403 (1995).
14. Diastereoselective reactions: (a) H. Takahashi and Y. Suzuki, Chem. Pharm. Bull., 31, 4295-4299 (1983) (b) Y. Yamamoto, S. Nishii, K. Maruyama, T. Komatsu, and W. Ito, J. Am. Chem. Soc., 108, 7778-7786 (1986) (c) D. Enders, H. Shubert, and C. Nübling, Angew. Chem. Int. Ed. Engl., 25, 1109-1110 (1986) (d) C. Boga, D. Savoia, and A. Umani-Ronchi, Tetrahedron: Asymmetry, 1, 291-294 (1990) (e) S. Laschat and H. Kunz, J. Org. Chem., 56, 5883-5889 (1991) (f) Y. Ukaji, T. Watai, T. Sumi, and T. Fujisawa, Chem. Lett., 1991, 1555-1558 (g) S. E. Denmark, J. P. Edwards, and O. Nicaise, J. Org. Chem., 58, 569-578 (1993) (h) T. -K. Yang, R. -Y. Chen, D. -S. Lee, W. -S. Peng, Y. -Z. Jiang, A. -Q. Mi, and T. -T. Jong, J. Org. Chem., 59, 914-921 (1994) (i) H. Suzuki, S. Aoyagi, and C. Kibayashi, Tetrahedron Lett., 36, 6709-6712 (1995) (j) D. S. Brown, P.T. Gallagher, A. P. Lightfoot, C. J. Moody, A. M. Z. Slawin, and E. Swann, Tetrahedron, 51, 11473-11488 (1995) (k) K. Higashiyama, H. Fujikura, and H. Takahashi, Chem. Pharm. Bull., 43, 722-728 (1995) Enantioselective reactions: (l) K. Tomioka, M. Shindo, and K. Koga, J. Am. Chem. Soc., 111, 8266-8268 (1989) (m) K. Tomioka, I. Inoue, M. Shindo, and K. Koga, Tetrahedron Lett., 31, 6681-6684 (1990) (n) K. Tomioka, I. Inoue, M. Shindo, and K. Koga, Tetrahedron Lett., 32, 3095-3098 (1991) (o) S. Itsuno, H. Yanaka, C. Hachisuka, and K. Ito, J. Chem. Soc., Perkin Trans. 1, 1991, 1341-1342 (p) K. Soai, T. Hatanaka, and T. Miyazawa, J. Chem. Soc., Chem. Commun., 1992, 1097-1098 (q) I. Inoue, M. Shindo, K. Koga, and K. Tomioka, Tetrahedron: Asymmetry, 4, 1603-1606 (1993) (r) I. Inoue, M. Shindo, K. Koga, and K. Tomioka, Tetrahedron, 50, 4429-4438 (1994) (s) S. E. Denmark, N. Nakajima, and O. J.-C. Nicaise, J. Am. Chem. Soc., 116, 8797-8798 (1994) (t) I. Inoue, M. Shindo, K. Koga, M. Kanai, and K. Tomioka, Tetrahedron: Asymmetry, 6, 2527-2533 (1995) Intramolecular reactions: (u) H. Waldmann, G. Schmidt, H. Henke, and M. Burkard, Angew. Chem. Int. Ed. Engl., 34, 2402-2403 (1995).
15. Diastereoselective reactions: (a) H. Takahashi and Y. Suzuki, Chem. Pharm. Bull., 31, 4295-4299 (1983) (b) Y. Yamamoto, S. Nishii, K. Maruyama, T. Komatsu, and W. Ito, J. Am. Chem. Soc., 108, 7778-7786 (1986) (c) D. Enders, H. Shubert, and C. Nübling, Angew. Chem. Int. Ed. Engl., 25, 1109-1110 (1986) (d) C. Boga, D. Savoia, and A. Umani-Ronchi, Tetrahedron: Asymmetry, 1, 291-294 (1990) (e) S. Laschat and H. Kunz, J. Org. Chem., 56, 5883-5889 (1991) (f) Y. Ukaji, T. Watai, T. Sumi, and T. Fujisawa, Chem. Lett., 1991, 1555-1558 (g) S. E. Denmark, J. P. Edwards, and O. Nicaise, J. Org. Chem., 58, 569-578 (1993) (h) T. -K. Yang, R. -Y. Chen, D. -S. Lee, W. -S. Peng, Y. -Z. Jiang, A. -Q. Mi, and T. -T. Jong, J. Org. Chem., 59, 914-921 (1994) (i) H. Suzuki, S. Aoyagi, and C. Kibayashi, Tetrahedron Lett., 36, 6709-6712 (1995) (j) D. S. Brown, P.T. Gallagher, A. P. Lightfoot, C. J. Moody, A. M. Z. Slawin, and E. Swann, Tetrahedron, 51, 11473-11488 (1995) (k) K. Higashiyama, H. Fujikura, and H. Takahashi, Chem. Pharm. Bull., 43, 722-728 (1995) Enantioselective reactions: (l) K. Tomioka, M. Shindo, and K. Koga, J. Am. Chem. Soc., 111, 8266-8268 (1989) (m) K. Tomioka, I. Inoue, M. Shindo, and K. Koga, Tetrahedron Lett., 31, 6681-6684 (1990) (n) K. Tomioka, I. Inoue, M. Shindo, and K. Koga, Tetrahedron Lett., 32, 3095-3098 (1991) (o) S. Itsuno, H. Yanaka, C. Hachisuka, and K. Ito, J. Chem. Soc., Perkin Trans. 1, 1991, 1341-1342 (p) K. Soai, T. Hatanaka, and T. Miyazawa, J. Chem. Soc., Chem. Commun., 1992, 1097-1098 (q) I. Inoue, M. Shindo, K. Koga, and K. Tomioka, Tetrahedron: Asymmetry, 4, 1603-1606 (1993) (r) I. Inoue, M. Shindo, K. Koga, and K. Tomioka, Tetrahedron, 50, 4429-4438 (1994) (s) S. E. Denmark, N. Nakajima, and O. J.-C. Nicaise, J. Am. Chem. Soc., 116, 8797-8798 (1994) (t) I. Inoue, M. Shindo, K. Koga, M. Kanai, and K. Tomioka, Tetrahedron: Asymmetry, 6, 2527-2533 (1995) Intramolecular reactions: (u) H. Waldmann, G. Schmidt, H. Henke, and M. Burkard, Angew. Chem. Int. Ed. Engl., 34, 2402-2403 (1995).
16. Diastereoselective reactions: (a) H. Takahashi and Y. Suzuki, Chem. Pharm. Bull., 31, 4295-4299 (1983) (b) Y. Yamamoto, S. Nishii, K. Maruyama, T. Komatsu, and W. Ito, J. Am. Chem. Soc., 108, 7778-7786 (1986) (c) D. Enders, H. Shubert, and C. Nübling, Angew. Chem. Int. Ed. Engl., 25, 1109-1110 (1986) (d) C. Boga, D. Savoia, and A. Umani-Ronchi, Tetrahedron: Asymmetry, 1, 291-294 (1990) (e) S. Laschat and H. Kunz, J. Org. Chem., 56, 5883-5889 (1991) (f) Y. Ukaji, T. Watai, T. Sumi, and T. Fujisawa, Chem. Lett., 1991, 1555-1558 (g) S. E. Denmark, J. P. Edwards, and O. Nicaise, J. Org. Chem., 58, 569-578 (1993) (h) T. -K. Yang, R. -Y. Chen, D. -S. Lee, W. -S. Peng, Y. -Z. Jiang, A. -Q. Mi, and T. -T. Jong, J. Org. Chem., 59, 914-921 (1994) (i) H. Suzuki, S. Aoyagi, and C. Kibayashi, Tetrahedron Lett., 36, 6709-6712 (1995) (j) D. S. Brown, P.T. Gallagher, A. P. Lightfoot, C. J. Moody, A. M. Z. Slawin, and E. Swann, Tetrahedron, 51, 11473-11488 (1995) (k) K. Higashiyama, H. Fujikura, and H. Takahashi, Chem. Pharm. Bull., 43, 722-728 (1995) Enantioselective reactions: (l) K. Tomioka, M. Shindo, and K. Koga, J. Am. Chem. Soc., 111, 8266-8268 (1989) (m) K. Tomioka, I. Inoue, M. Shindo, and K. Koga, Tetrahedron Lett., 31, 6681-6684 (1990) (n) K. Tomioka, I. Inoue, M. Shindo, and K. Koga, Tetrahedron Lett., 32, 3095-3098 (1991) (o) S. Itsuno, H. Yanaka, C. Hachisuka, and K. Ito, J. Chem. Soc., Perkin Trans. 1, 1991, 1341-1342 (p) K. Soai, T. Hatanaka, and T. Miyazawa, J. Chem. Soc., Chem. Commun., 1992, 1097-1098 (q) I. Inoue, M. Shindo, K. Koga, and K. Tomioka, Tetrahedron: Asymmetry, 4, 1603-1606 (1993) (r) I. Inoue, M. Shindo, K. Koga, and K. Tomioka, Tetrahedron, 50, 4429-4438 (1994) (s) S. E. Denmark, N. Nakajima, and O. J.-C. Nicaise, J. Am. Chem. Soc., 116, 8797-8798 (1994) (t) I. Inoue, M. Shindo, K. Koga, M. Kanai, and K. Tomioka, Tetrahedron: Asymmetry, 6, 2527-2533 (1995) Intramolecular reactions: (u) H. Waldmann, G. Schmidt, H. Henke, and M. Burkard, Angew. Chem. Int. Ed. Engl., 34, 2402-2403 (1995).
17. Diastereoselective reactions: (a) H. Takahashi and Y. Suzuki, Chem. Pharm. Bull., 31, 4295-4299 (1983) (b) Y. Yamamoto, S. Nishii, K. Maruyama, T. Komatsu, and W. Ito, J. Am. Chem. Soc., 108, 7778-7786 (1986) (c) D. Enders, H. Shubert, and C. Nübling, Angew. Chem. Int. Ed. Engl., 25, 1109-1110 (1986) (d) C. Boga, D. Savoia, and A. Umani-Ronchi, Tetrahedron: Asymmetry, 1, 291-294 (1990) (e) S. Laschat and H. Kunz, J. Org. Chem., 56, 5883-5889 (1991) (f) Y. Ukaji, T. Watai, T. Sumi, and T. Fujisawa, Chem. Lett., 1991, 1555-1558 (g) S. E. Denmark, J. P. Edwards, and O. Nicaise, J. Org. Chem., 58, 569-578 (1993) (h) T. -K. Yang, R. -Y. Chen, D. -S. Lee, W. -S. Peng, Y. -Z. Jiang, A. -Q. Mi, and T. -T. Jong, J. Org. Chem., 59, 914-921 (1994) (i) H. Suzuki, S. Aoyagi, and C. Kibayashi, Tetrahedron Lett., 36, 6709-6712 (1995) (j) D. S. Brown, P.T. Gallagher, A. P. Lightfoot, C. J. Moody, A. M. Z. Slawin, and E. Swann, Tetrahedron, 51, 11473-11488 (1995) (k) K. Higashiyama, H. Fujikura, and H. Takahashi, Chem. Pharm. Bull., 43, 722-728 (1995) Enantioselective reactions: (l) K. Tomioka, M. Shindo, and K. Koga, J. Am. Chem. Soc., 111, 8266-8268 (1989) (m) K. Tomioka, I. Inoue, M. Shindo, and K. Koga, Tetrahedron Lett., 31, 6681-6684 (1990) (n) K. Tomioka, I. Inoue, M. Shindo, and K. Koga, Tetrahedron Lett., 32, 3095-3098 (1991) (o) S. Itsuno, H. Yanaka, C. Hachisuka, and K. Ito, J. Chem. Soc., Perkin Trans. 1, 1991, 1341-1342 (p) K. Soai, T. Hatanaka, and T. Miyazawa, J. Chem. Soc., Chem. Commun., 1992, 1097-1098 (q) I. Inoue, M. Shindo, K. Koga, and K. Tomioka, Tetrahedron: Asymmetry, 4, 1603-1606 (1993) (r) I. Inoue, M. Shindo, K. Koga, and K. Tomioka, Tetrahedron, 50, 4429-4438 (1994) (s) S. E. Denmark, N. Nakajima, and O. J.-C. Nicaise, J. Am. Chem. Soc., 116, 8797-8798 (1994) (t) I. Inoue, M. Shindo, K. Koga, M. Kanai, and K. Tomioka, Tetrahedron: Asymmetry, 6, 2527-2533 (1995) Intramolecular reactions: (u) H. Waldmann, G. Schmidt, H. Henke, and M. Burkard, Angew. Chem. Int. Ed. Engl., 34, 2402-2403 (1995).
18. Diastereoselective reactions: (a) H. Takahashi and Y. Suzuki, Chem. Pharm. Bull., 31, 4295-4299 (1983) (b) Y. Yamamoto, S. Nishii, K. Maruyama, T. Komatsu, and W. Ito, J. Am. Chem. Soc., 108, 7778-7786 (1986) (c) D. Enders, H. Shubert, and C. Nübling, Angew. Chem. Int. Ed. Engl., 25, 1109-1110 (1986) (d) C. Boga, D. Savoia, and A. Umani-Ronchi, Tetrahedron: Asymmetry, 1, 291-294 (1990) (e) S. Laschat and H. Kunz, J. Org. Chem., 56, 5883-5889 (1991) (f) Y. Ukaji, T. Watai, T. Sumi, and T. Fujisawa, Chem. Lett., 1991, 1555-1558 (g) S. E. Denmark, J. P. Edwards, and O. Nicaise, J. Org. Chem., 58, 569-578 (1993) (h) T. -K. Yang, R. -Y. Chen, D. -S. Lee, W. -S. Peng, Y. -Z. Jiang, A. -Q. Mi, and T. -T. Jong, J. Org. Chem., 59, 914-921 (1994) (i) H. Suzuki, S. Aoyagi, and C. Kibayashi, Tetrahedron Lett., 36, 6709-6712 (1995) (j) D. S. Brown, P.T. Gallagher, A. P. Lightfoot, C. J. Moody, A. M. Z. Slawin, and E. Swann, Tetrahedron, 51, 11473-11488 (1995) (k) K. Higashiyama, H. Fujikura, and H. Takahashi, Chem. Pharm. Bull., 43, 722-728 (1995) Enantioselective reactions: (l) K. Tomioka, M. Shindo, and K. Koga, J. Am. Chem. Soc., 111, 8266-8268 (1989) (m) K. Tomioka, I. Inoue, M. Shindo, and K. Koga, Tetrahedron Lett., 31, 6681-6684 (1990) (n) K. Tomioka, I. Inoue, M. Shindo, and K. Koga, Tetrahedron Lett., 32, 3095-3098 (1991) (o) S. Itsuno, H. Yanaka, C. Hachisuka, and K. Ito, J. Chem. Soc., Perkin Trans. 1, 1991, 1341-1342 (p) K. Soai, T. Hatanaka, and T. Miyazawa, J. Chem. Soc., Chem. Commun., 1992, 1097-1098 (q) I. Inoue, M. Shindo, K. Koga, and K. Tomioka, Tetrahedron: Asymmetry, 4, 1603-1606 (1993) (r) I. Inoue, M. Shindo, K. Koga, and K. Tomioka, Tetrahedron, 50, 4429-4438 (1994) (s) S. E. Denmark, N. Nakajima, and O. J.-C. Nicaise, J. Am. Chem. Soc., 116, 8797-8798 (1994) (t) I. Inoue, M. Shindo, K. Koga, M. Kanai, and K. Tomioka, Tetrahedron: Asymmetry, 6, 2527-2533 (1995) Intramolecular reactions: (u) H. Waldmann, G. Schmidt, H. Henke, and M. Burkard, Angew. Chem. Int. Ed. Engl., 34, 2402-2403 (1995).
19. Diastereoselective reactions: (a) H. Takahashi and Y. Suzuki, Chem. Pharm. Bull., 31, 4295-4299 (1983) (b) Y. Yamamoto, S. Nishii, K. Maruyama, T. Komatsu, and W. Ito, J. Am. Chem. Soc., 108, 7778-7786 (1986) (c) D. Enders, H. Shubert, and C. Nübling, Angew. Chem. Int. Ed. Engl., 25, 1109-1110 (1986) (d) C. Boga, D. Savoia, and A. Umani-Ronchi, Tetrahedron: Asymmetry, 1, 291-294 (1990) (e) S. Laschat and H. Kunz, J. Org. Chem., 56, 5883-5889 (1991) (f) Y. Ukaji, T. Watai, T. Sumi, and T. Fujisawa, Chem. Lett., 1991, 1555-1558 (g) S. E. Denmark, J. P. Edwards, and O. Nicaise, J. Org. Chem., 58, 569-578 (1993) (h) T. -K. Yang, R. -Y. Chen, D. -S. Lee, W. -S. Peng, Y. -Z. Jiang, A. -Q. Mi, and T. -T. Jong, J. Org. Chem., 59, 914-921 (1994) (i) H. Suzuki, S. Aoyagi, and C. Kibayashi, Tetrahedron Lett., 36, 6709-6712 (1995) (j) D. S. Brown, P.T. Gallagher, A. P. Lightfoot, C. J. Moody, A. M. Z. Slawin, and E. Swann, Tetrahedron, 51, 11473-11488 (1995) (k) K. Higashiyama, H. Fujikura, and H. Takahashi, Chem. Pharm. Bull., 43, 722-728 (1995) Enantioselective reactions: (l) K. Tomioka, M. Shindo, and K. Koga, J. Am. Chem. Soc., 111, 8266-8268 (1989) (m) K. Tomioka, I. Inoue, M. Shindo, and K. Koga, Tetrahedron Lett., 31, 6681-6684 (1990) (n) K. Tomioka, I. Inoue, M. Shindo, and K. Koga, Tetrahedron Lett., 32, 3095-3098 (1991) (o) S. Itsuno, H. Yanaka, C. Hachisuka, and K. Ito, J. Chem. Soc., Perkin Trans. 1, 1991, 1341-1342 (p) K. Soai, T. Hatanaka, and T. Miyazawa, J. Chem. Soc., Chem. Commun., 1992, 1097-1098 (q) I. Inoue, M. Shindo, K. Koga, and K. Tomioka, Tetrahedron: Asymmetry, 4, 1603-1606 (1993) (r) I. Inoue, M. Shindo, K. Koga, and K. Tomioka, Tetrahedron, 50, 4429-4438 (1994) (s) S. E. Denmark, N. Nakajima, and O. J.-C. Nicaise, J. Am. Chem. Soc., 116, 8797-8798 (1994) (t) I. Inoue, M. Shindo, K. Koga, M. Kanai, and K. Tomioka, Tetrahedron: Asymmetry, 6, 2527-2533 (1995) Intramolecular reactions: (u) H. Waldmann, G. Schmidt, H. Henke, and M. Burkard, Angew. Chem. Int. Ed. Engl., 34, 2402-2403 (1995).
20. Diastereoselective reactions: (a) H. Takahashi and Y. Suzuki, Chem. Pharm. Bull., 31, 4295-4299 (1983) (b) Y. Yamamoto, S. Nishii, K. Maruyama, T. Komatsu, and W. Ito, J. Am. Chem. Soc., 108, 7778-7786 (1986) (c) D. Enders, H. Shubert, and C. Nübling, Angew. Chem. Int. Ed. Engl., 25, 1109-1110 (1986) (d) C. Boga, D. Savoia, and A. Umani-Ronchi, Tetrahedron: Asymmetry, 1, 291-294 (1990) (e) S. Laschat and H. Kunz, J. Org. Chem., 56, 5883-5889 (1991) (f) Y. Ukaji, T. Watai, T. Sumi, and T. Fujisawa, Chem. Lett., 1991, 1555-1558 (g) S. E. Denmark, J. P. Edwards, and O. Nicaise, J. Org. Chem., 58, 569-578 (1993) (h) T. -K. Yang, R. -Y. Chen, D. -S. Lee, W. -S. Peng, Y. -Z. Jiang, A. -Q. Mi, and T. -T. Jong, J. Org. Chem., 59, 914-921 (1994) (i) H. Suzuki, S. Aoyagi, and C. Kibayashi, Tetrahedron Lett., 36, 6709-6712 (1995) (j) D. S. Brown, P.T. Gallagher, A. P. Lightfoot, C. J. Moody, A. M. Z. Slawin, and E. Swann, Tetrahedron, 51, 11473-11488 (1995) (k) K. Higashiyama, H. Fujikura, and H. Takahashi, Chem. Pharm. Bull., 43, 722-728 (1995) Enantioselective reactions: (l) K. Tomioka, M. Shindo, and K. Koga, J. Am. Chem. Soc., 111, 8266-8268 (1989) (m) K. Tomioka, I. Inoue, M. Shindo, and K. Koga, Tetrahedron Lett., 31, 6681-6684 (1990) (n) K. Tomioka, I. Inoue, M. Shindo, and K. Koga, Tetrahedron Lett., 32, 3095-3098 (1991) (o) S. Itsuno, H. Yanaka, C. Hachisuka, and K. Ito, J. Chem. Soc., Perkin Trans. 1, 1991, 1341-1342 (p) K. Soai, T. Hatanaka, and T. Miyazawa, J. Chem. Soc., Chem. Commun., 1992, 1097-1098 (q) I. Inoue, M. Shindo, K. Koga, and K. Tomioka, Tetrahedron: Asymmetry, 4, 1603-1606 (1993) (r) I. Inoue, M. Shindo, K. Koga, and K. Tomioka, Tetrahedron, 50, 4429-4438 (1994) (s) S. E. Denmark, N. Nakajima, and O. J.-C. Nicaise, J. Am. Chem. Soc., 116, 8797-8798 (1994) (t) I. Inoue, M. Shindo, K. Koga, M. Kanai, and K. Tomioka, Tetrahedron: Asymmetry, 6, 2527-2533 (1995) Intramolecular reactions: (u) H. Waldmann, G. Schmidt, H. Henke, and M. Burkard, Angew. Chem. Int. Ed. Engl., 34, 2402-2403 (1995).
21. Diastereoselective reactions: (a) H. Takahashi and Y. Suzuki, Chem. Pharm. Bull., 31, 4295-4299 (1983) (b) Y. Yamamoto, S. Nishii, K. Maruyama, T. Komatsu, and W. Ito, J. Am. Chem. Soc., 108, 7778-7786 (1986) (c) D. Enders, H. Shubert, and C. Nübling, Angew. Chem. Int. Ed. Engl., 25, 1109-1110 (1986) (d) C. Boga, D. Savoia, and A. Umani-Ronchi, Tetrahedron: Asymmetry, 1, 291-294 (1990) (e) S. Laschat and H. Kunz, J. Org. Chem., 56, 5883-5889 (1991) (f) Y. Ukaji, T. Watai, T. Sumi, and T. Fujisawa, Chem. Lett., 1991, 1555-1558 (g) S. E. Denmark, J. P. Edwards, and O. Nicaise, J. Org. Chem., 58, 569-578 (1993) (h) T. -K. Yang, R. -Y. Chen, D. -S. Lee, W. -S. Peng, Y. -Z. Jiang, A. -Q. Mi, and T. -T. Jong, J. Org. Chem., 59, 914-921 (1994) (i) H. Suzuki, S. Aoyagi, and C. Kibayashi, Tetrahedron Lett., 36, 6709-6712 (1995) (j) D. S. Brown, P.T. Gallagher, A. P. Lightfoot, C. J. Moody, A. M. Z. Slawin, and E. Swann, Tetrahedron, 51, 11473-11488 (1995) (k) K. Higashiyama, H. Fujikura, and H. Takahashi, Chem. Pharm. Bull., 43, 722-728 (1995) Enantioselective reactions: (l) K. Tomioka, M. Shindo, and K. Koga, J. Am. Chem. Soc., 111, 8266-8268 (1989) (m) K. Tomioka, I. Inoue, M. Shindo, and K. Koga, Tetrahedron Lett., 31, 6681-6684 (1990) (n) K. Tomioka, I. Inoue, M. Shindo, and K. Koga, Tetrahedron Lett., 32, 3095-3098 (1991) (o) S. Itsuno, H. Yanaka, C. Hachisuka, and K. Ito, J. Chem. Soc., Perkin Trans. 1, 1991, 1341-1342 (p) K. Soai, T. Hatanaka, and T. Miyazawa, J. Chem. Soc., Chem. Commun., 1992, 1097-1098 (q) I. Inoue, M. Shindo, K. Koga, and K. Tomioka, Tetrahedron: Asymmetry, 4, 1603-1606 (1993) (r) I. Inoue, M. Shindo, K. Koga, and K. Tomioka, Tetrahedron, 50, 4429-4438 (1994) (s) S. E. Denmark, N. Nakajima, and O. J.-C. Nicaise, J. Am. Chem. Soc., 116, 8797-8798 (1994) (t) I. Inoue, M. Shindo, K. Koga, M. Kanai, and K. Tomioka, Tetrahedron: Asymmetry, 6, 2527-2533 (1995) Intramolecular reactions: (u) H. Waldmann, G. Schmidt, H. Henke, and M. Burkard, Angew. Chem. Int. Ed. Engl., 34, 2402-2403 (1995).
22. (a) T. Kawate, M. Nakagawa, T. Kakikawa, and T. Hino, Tetrahedron: Asymmetry, 3, 227-230 (1992)
23. (b) M. Nakagawa, T. Kawate, T. Kakikawa, H. Yamada, T. Matsui, and T. Hino, Tetrahedron, 49, 1739-1748 (1993).
24. All new compounds are characterized spectroscopically (nmr, ir, low mass, high mass and/or elemental analysis).
25. H) of alkylation products used for calculation of diastereomer ratio: PhCHN 3a 3.35 3b 3.76 4a 3.58 4b 3.89 5a 3.07 5b 3.61 NCHMe 4.36 4.48 4.39 4.58 tBuCHN 6a 2.43 6b 3.83 7a 3.17 7b 3.63 NCHMe 4.64 5.22
26. D -12.85 (EtOH).