A novel highly effective chiral lithium amide for catalytic enantioselective deprotonation of meso-epoxides

Tetrahedron Letters

Volumn 38, Issue 36, 1997, Pages 6425-6428

  Asami, Masatoshi ^a   Suga, Takashi ^a   Honda, Kiyoshi ^a   Inoue, Seiichi ^a  

^a YOKOHAMA NATIONAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; CYCLOALKANOL DERIVATIVE; CYCLOHEXENE DERIVATIVE;

ARTICLE; CATALYSIS; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030864050     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01487-1     Document Type: Article

References (18)

1. Review: (a) P. J. Cox, P.J.; Simpkins, N. S. Tetrahedron: Asymmetry 1991, 2, 1-26. (b) Koga, K. Pure & Applied Chem. 1994, 66, 1487-1492. (c) Koga, K., Shindo, M. J. Synth. Org. Chem., Jpn. 1995, 53, 1021-1032. (d) Asami, M. J. Synth. Org. Chem., Jpn. 1996, 54, 188-199. (e) Simpkins, N. S. Pure & Applied Chem. 1996, 68, 691-694. (f) Hodgson, D. M.; Gibbs, A. R.; Lee, G. P. Tetrahedron 1996, 52, 14361-14384. Recent examples: (g) O'Brien, P.; Fiumana, A. Tetrahedron Lett., 1996, 37, 8057- 8058. (h) Yamashita, T.; Sato, D.; Kiyoto, T.; Kumar, A.; Koga, K. Tetrahedron Lett., 1996, 37, 8195- 8198. (i) Hodgson, D. M.; Marriott, R. Tetrahedron: Asymmetry 1997, 8, 519-521. (j) Tierney, J. P.; Alexakis, A.; Mangeney, P. Tetrahedron: Asymmetry 1997, 8, 1019-1022. (k) Schwink, L.; Knochel, P. Tetrahedron Lett., 1997, 38, 3711-3714.
2. Review: (a) P. J. Cox, P.J.; Simpkins, N. S. Tetrahedron: Asymmetry 1991, 2, 1-26. (b) Koga, K. Pure & Applied Chem. 1994, 66, 1487-1492. (c) Koga, K., Shindo, M. J. Synth. Org. Chem., Jpn. 1995, 53, 1021-1032. (d) Asami, M. J. Synth. Org. Chem., Jpn. 1996, 54, 188-199. (e) Simpkins, N. S. Pure & Applied Chem. 1996, 68, 691-694. (f) Hodgson, D. M.; Gibbs, A. R.; Lee, G. P. Tetrahedron 1996, 52, 14361-14384. Recent examples: (g) O'Brien, P.; Fiumana, A. Tetrahedron Lett., 1996, 37, 8057- 8058. (h) Yamashita, T.; Sato, D.; Kiyoto, T.; Kumar, A.; Koga, K. Tetrahedron Lett., 1996, 37, 8195- 8198. (i) Hodgson, D. M.; Marriott, R. Tetrahedron: Asymmetry 1997, 8, 519-521. (j) Tierney, J. P.; Alexakis, A.; Mangeney, P. Tetrahedron: Asymmetry 1997, 8, 1019-1022. (k) Schwink, L.; Knochel, P. Tetrahedron Lett., 1997, 38, 3711-3714.
3. Review: (a) P. J. Cox, P.J.; Simpkins, N. S. Tetrahedron: Asymmetry 1991, 2, 1-26. (b) Koga, K. Pure & Applied Chem. 1994, 66, 1487-1492. (c) Koga, K., Shindo, M. J. Synth. Org. Chem., Jpn. 1995, 53, 1021-1032. (d) Asami, M. J. Synth. Org. Chem., Jpn. 1996, 54, 188-199. (e) Simpkins, N. S. Pure & Applied Chem. 1996, 68, 691-694. (f) Hodgson, D. M.; Gibbs, A. R.; Lee, G. P. Tetrahedron 1996, 52, 14361-14384. Recent examples: (g) O'Brien, P.; Fiumana, A. Tetrahedron Lett., 1996, 37, 8057- 8058. (h) Yamashita, T.; Sato, D.; Kiyoto, T.; Kumar, A.; Koga, K. Tetrahedron Lett., 1996, 37, 8195- 8198. (i) Hodgson, D. M.; Marriott, R. Tetrahedron: Asymmetry 1997, 8, 519-521. (j) Tierney, J. P.; Alexakis, A.; Mangeney, P. Tetrahedron: Asymmetry 1997, 8, 1019-1022. (k) Schwink, L.; Knochel, P. Tetrahedron Lett., 1997, 38, 3711-3714.
4. Review: (a) P. J. Cox, P.J.; Simpkins, N. S. Tetrahedron: Asymmetry 1991, 2, 1-26. (b) Koga, K. Pure & Applied Chem. 1994, 66, 1487-1492. (c) Koga, K., Shindo, M. J. Synth. Org. Chem., Jpn. 1995, 53, 1021-1032. (d) Asami, M. J. Synth. Org. Chem., Jpn. 1996, 54, 188-199. (e) Simpkins, N. S. Pure & Applied Chem. 1996, 68, 691-694. (f) Hodgson, D. M.; Gibbs, A. R.; Lee, G. P. Tetrahedron 1996, 52, 14361-14384. Recent examples: (g) O'Brien, P.; Fiumana, A. Tetrahedron Lett., 1996, 37, 8057- 8058. (h) Yamashita, T.; Sato, D.; Kiyoto, T.; Kumar, A.; Koga, K. Tetrahedron Lett., 1996, 37, 8195- 8198. (i) Hodgson, D. M.; Marriott, R. Tetrahedron: Asymmetry 1997, 8, 519-521. (j) Tierney, J. P.; Alexakis, A.; Mangeney, P. Tetrahedron: Asymmetry 1997, 8, 1019-1022. (k) Schwink, L.; Knochel, P. Tetrahedron Lett., 1997, 38, 3711-3714.
5. Review: (a) P. J. Cox, P.J.; Simpkins, N. S. Tetrahedron: Asymmetry 1991, 2, 1-26. (b) Koga, K. Pure & Applied Chem. 1994, 66, 1487-1492. (c) Koga, K., Shindo, M. J. Synth. Org. Chem., Jpn. 1995, 53, 1021-1032. (d) Asami, M. J. Synth. Org. Chem., Jpn. 1996, 54, 188-199. (e) Simpkins, N. S. Pure & Applied Chem. 1996, 68, 691-694. (f) Hodgson, D. M.; Gibbs, A. R.; Lee, G. P. Tetrahedron 1996, 52, 14361-14384. Recent examples: (g) O'Brien, P.; Fiumana, A. Tetrahedron Lett., 1996, 37, 8057- 8058. (h) Yamashita, T.; Sato, D.; Kiyoto, T.; Kumar, A.; Koga, K. Tetrahedron Lett., 1996, 37, 8195- 8198. (i) Hodgson, D. M.; Marriott, R. Tetrahedron: Asymmetry 1997, 8, 519-521. (j) Tierney, J. P.; Alexakis, A.; Mangeney, P. Tetrahedron: Asymmetry 1997, 8, 1019-1022. (k) Schwink, L.; Knochel, P. Tetrahedron Lett., 1997, 38, 3711-3714.
6. Review: (a) P. J. Cox, P.J.; Simpkins, N. S. Tetrahedron: Asymmetry 1991, 2, 1-26. (b) Koga, K. Pure & Applied Chem. 1994, 66, 1487-1492. (c) Koga, K., Shindo, M. J. Synth. Org. Chem., Jpn. 1995, 53, 1021-1032. (d) Asami, M. J. Synth. Org. Chem., Jpn. 1996, 54, 188-199. (e) Simpkins, N. S. Pure & Applied Chem. 1996, 68, 691-694. (f) Hodgson, D. M.; Gibbs, A. R.; Lee, G. P. Tetrahedron 1996, 52, 14361-14384. Recent examples: (g) O'Brien, P.; Fiumana, A. Tetrahedron Lett., 1996, 37, 8057- 8058. (h) Yamashita, T.; Sato, D.; Kiyoto, T.; Kumar, A.; Koga, K. Tetrahedron Lett., 1996, 37, 8195- 8198. (i) Hodgson, D. M.; Marriott, R. Tetrahedron: Asymmetry 1997, 8, 519-521. (j) Tierney, J. P.; Alexakis, A.; Mangeney, P. Tetrahedron: Asymmetry 1997, 8, 1019-1022. (k) Schwink, L.; Knochel, P. Tetrahedron Lett., 1997, 38, 3711-3714.
7. Review: (a) P. J. Cox, P.J.; Simpkins, N. S. Tetrahedron: Asymmetry 1991, 2, 1-26. (b) Koga, K. Pure & Applied Chem. 1994, 66, 1487-1492. (c) Koga, K., Shindo, M. J. Synth. Org. Chem., Jpn. 1995, 53, 1021-1032. (d) Asami, M. J. Synth. Org. Chem., Jpn. 1996, 54, 188-199. (e) Simpkins, N. S. Pure & Applied Chem. 1996, 68, 691-694. (f) Hodgson, D. M.; Gibbs, A. R.; Lee, G. P. Tetrahedron 1996, 52, 14361-14384. Recent examples: (g) O'Brien, P.; Fiumana, A. Tetrahedron Lett., 1996, 37, 8057-8058. (h) Yamashita, T.; Sato, D.; Kiyoto, T.; Kumar, A.; Koga, K. Tetrahedron Lett., 1996, 37, 8195- 8198. (i) Hodgson, D. M.; Marriott, R. Tetrahedron: Asymmetry 1997, 8, 519-521. (j) Tierney, J. P.; Alexakis, A.; Mangeney, P. Tetrahedron: Asymmetry 1997, 8, 1019-1022. (k) Schwink, L.; Knochel, P. Tetrahedron Lett., 1997, 38, 3711-3714.
8. Review: (a) P. J. Cox, P.J.; Simpkins, N. S. Tetrahedron: Asymmetry 1991, 2, 1-26. (b) Koga, K. Pure & Applied Chem. 1994, 66, 1487-1492. (c) Koga, K., Shindo, M. J. Synth. Org. Chem., Jpn. 1995, 53, 1021-1032. (d) Asami, M. J. Synth. Org. Chem., Jpn. 1996, 54, 188-199. (e) Simpkins, N. S. Pure & Applied Chem. 1996, 68, 691-694. (f) Hodgson, D. M.; Gibbs, A. R.; Lee, G. P. Tetrahedron 1996, 52, 14361-14384. Recent examples: (g) O'Brien, P.; Fiumana, A. Tetrahedron Lett., 1996, 37, 8057- 8058. (h) Yamashita, T.; Sato, D.; Kiyoto, T.; Kumar, A.; Koga, K. Tetrahedron Lett., 1996, 37, 8195-8198. (i) Hodgson, D. M.; Marriott, R. Tetrahedron: Asymmetry 1997, 8, 519-521. (j) Tierney, J. P.; Alexakis, A.; Mangeney, P. Tetrahedron: Asymmetry 1997, 8, 1019-1022. (k) Schwink, L.; Knochel, P. Tetrahedron Lett., 1997, 38, 3711-3714.
9. Review: (a) P. J. Cox, P.J.; Simpkins, N. S. Tetrahedron: Asymmetry 1991, 2, 1-26. (b) Koga, K. Pure & Applied Chem. 1994, 66, 1487-1492. (c) Koga, K., Shindo, M. J. Synth. Org. Chem., Jpn. 1995, 53, 1021-1032. (d) Asami, M. J. Synth. Org. Chem., Jpn. 1996, 54, 188-199. (e) Simpkins, N. S. Pure & Applied Chem. 1996, 68, 691-694. (f) Hodgson, D. M.; Gibbs, A. R.; Lee, G. P. Tetrahedron 1996, 52, 14361-14384. Recent examples: (g) O'Brien, P.; Fiumana, A. Tetrahedron Lett., 1996, 37, 8057- 8058. (h) Yamashita, T.; Sato, D.; Kiyoto, T.; Kumar, A.; Koga, K. Tetrahedron Lett., 1996, 37, 8195- 8198. (i) Hodgson, D. M.; Marriott, R. Tetrahedron: Asymmetry 1997, 8, 519-521. (j) Tierney, J. P.; Alexakis, A.; Mangeney, P. Tetrahedron: Asymmetry 1997, 8, 1019-1022. (k) Schwink, L.; Knochel, P. Tetrahedron Lett., 1997, 38, 3711-3714.
10. Review: (a) P. J. Cox, P.J.; Simpkins, N. S. Tetrahedron: Asymmetry 1991, 2, 1-26. (b) Koga, K. Pure & Applied Chem. 1994, 66, 1487-1492. (c) Koga, K., Shindo, M. J. Synth. Org. Chem., Jpn. 1995, 53, 1021-1032. (d) Asami, M. J. Synth. Org. Chem., Jpn. 1996, 54, 188-199. (e) Simpkins, N. S. Pure & Applied Chem. 1996, 68, 691-694. (f) Hodgson, D. M.; Gibbs, A. R.; Lee, G. P. Tetrahedron 1996, 52, 14361-14384. Recent examples: (g) O'Brien, P.; Fiumana, A. Tetrahedron Lett., 1996, 37, 8057- 8058. (h) Yamashita, T.; Sato, D.; Kiyoto, T.; Kumar, A.; Koga, K. Tetrahedron Lett., 1996, 37, 8195- 8198. (i) Hodgson, D. M.; Marriott, R. Tetrahedron: Asymmetry 1997, 8, 519-521. (j) Tierney, J. P.; Alexakis, A.; Mangeney, P. Tetrahedron: Asymmetry 1997, 8, 1019-1022. (k) Schwink, L.; Knochel, P. Tetrahedron Lett., 1997, 38, 3711-3714.
11. Review: (a) P. J. Cox, P.J.; Simpkins, N. S. Tetrahedron: Asymmetry 1991, 2, 1-26. (b) Koga, K. Pure & Applied Chem. 1994, 66, 1487-1492. (c) Koga, K., Shindo, M. J. Synth. Org. Chem., Jpn. 1995, 53, 1021-1032. (d) Asami, M. J. Synth. Org. Chem., Jpn. 1996, 54, 188-199. (e) Simpkins, N. S. Pure & Applied Chem. 1996, 68, 691-694. (f) Hodgson, D. M.; Gibbs, A. R.; Lee, G. P. Tetrahedron 1996, 52, 14361-14384. Recent examples: (g) O'Brien, P.; Fiumana, A. Tetrahedron Lett., 1996, 37, 8057- 8058. (h) Yamashita, T.; Sato, D.; Kiyoto, T.; Kumar, A.; Koga, K. Tetrahedron Lett., 1996, 37, 8195- 8198. (i) Hodgson, D. M.; Marriott, R. Tetrahedron: Asymmetry 1997, 8, 519-521. (j) Tierney, J. P.; Alexakis, A.; Mangeney, P. Tetrahedron: Asymmetry 1997, 8, 1019-1022. (k) Schwink, L.; Knochel, P. Tetrahedron Lett., 1997, 38, 3711-3714.
12. 4
13. (a) Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley & Sons: New York, 1994.
14. (b) Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993.
15. Asami, M.; Ishizaki, T.; Inoue, S. Tetrahedron: Asymmetry 1994, 5, 793-796.
16. 14 (dipicrate of 3; mp 170.6-171.8°C): C, 45.05; H, 4.54; N, 16.81. Found; C, 44.83; H, 4.54; N, 16.59.
17. Asami, M. Bull. Chem. Soc. Jpn., 1990, 63, 721-727.
18. 4 and then concentrated in vacuo. The crude product was chromatographed on silica gel to give (S)-2-cyclohexenyl benzoate. The ee was determined by HPLC using a chiral column. Pure 2-cyclohexen-1-ol was obtained by the hydrolysis of the benzoate ester with sodium hydroxide in methanol.