Stereoselective reactions. 29. Lithium-hydrogen interchange between achiral tridentate lithium amides and chiral bidentate amines. An approach to catalytic enantioselective

Tetrahedron

Volumn 53, Issue 50, 1997, Pages 16987-16998

  Yamashita, Toyoharu ^a   Sato, Daisaku ^a   Kiyoto, Taro ^a   Kumar, Arvind ^a   Koga, Kenji ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; ENANTIOMER; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0030732772     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10144-2     Document Type: Article

References (42)

1. Part 28: Aoki, K.; Tomioka, K.; Noguchi, H.; Koga, K. Tetrahedron, in press.
2. a) Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry, Part B: Reactions and Synthesis; Plenum Press: New York, 1990; Chapters 1 and 2.
3. b) Mekelburger, H, B.; Wilcox, C. S. Comprehensive Organic Synthesis; Vol. 2, Trost, B. M.; Fleming, I., Ed.; Pergamon Press, Oxford, 1991, Chapter 1.4.
4. c) Caine, D. Comprehensive Organic Synthesis; Vol. 3, Trost, B. M.; Fleming, I., Ed.; Pergamon Press, Oxford, 1991, Chapter 1.1.
5. For reviews: a) Koga, K. J. Synth. Org. Chem., Jpn. 1990, 48, 463-475.
6. b) Cox, P. J.; Simpkins, N. S. Tetrahedron: Asymmetry 1991, 2, 1-26.
7. c) Waldmann, H. Nachr. Chem. Tech. Lab. 1991, 39, 413-418.
8. d) Koga, K. Pure Appl. Chem. 1994, 66, 1487-1492.
9. e) Koga, K.; Shindo, M. J. Synth. Org. Chem., Jpn. 1995, 52, 1021-1032.
10. f) Simpkins, N. S. Pure Appl. Chem. 1996, 68, 691-694.
11. g) Simpkins, N. S. Advanced Asymmetric Synthesis; Stephenson, G. R. Ed.; Chapman & Hall: London, 1996; pp. 111-125.
12. Corey, E. J.; Gross, A. W. Tetrahedron Lett. 1984, 25, 495-498.
13. a) Shirai, R.; Tanaka, M.; Koga, K. J. Am. Chem. Soc. 1986, 108, 543-545.
14. b) Sato, D.; Kawasaki, H.; Shimada, I.; Arata, Y.; Okamura, K.; Date, T.; Koga, K. J. Am. Chem. Soc. 1992, 114, 761-763.
15. c) Aoki, K.; Noguchi, H.; Tomioka, K.; Koga, K. Tetrahedron Lett. 1993, 34, 5105-5108.
16. d) Sugasawa, K.; Shindo, M.; Noguchi, H.; Tomioka, K.; Koga, K. Tetrahedron Lett. 1996, 37, 7377-7380.
17. e) Toriyama, M.; Sugasawa, K.; Shindo, M.; Tokutake, N.; Koga, K. Tetrahedron Lett. 1997, 38, 567-570.
18. f) Aoki, K.; Koga, K. Tetrahedron Lett. 1997, 38, 2505-2506.
19. g) Shirai, R.; Sato, D.; Aoki, K.; Tanaka, M.; Kawasaki, H.; Koga, K. Tetrahedron, 1997, 53, 5963-5972.
20. h) Sato, D,; Kawasaki, H.; Shimada, I.; Arata, Y.; Okamura, K.; Date, T.; Koga, K. Tetrahedron 1997, 53, 7191-7200.
21. i) Sato, D.; Kawasaki, H.; Koga, K. Chem. Pharm. Bull. 1997, 45, 1399-1402.
22. j) Chatani, H.; Nakajima, M.; Kawasaki, H.; Koga, K. Heterocycles, in press.
23. A part of this paper is reported as a communication: Yamashita, T.; Sato, D.; Kiyoto, T.; Kumar, A.; Koga, K. Tetrahedron Lett. 1996, 37, 8195-8198.
24. EQ method was employed because deprotonation of 1 by fluorine-containing chiral lithium amides under IQ method gave 4 in lower chemical yields due to the formation of N-silylated chiral amines to some extent.
25. It is conceivable that the tetramethylpiperidino group in 5f is too bulky to work efficiently as an internal ligation site for the lithium.
26. a) Ireland, R. E.; Mueller, R. H.; Willard, A. K. J. Am. Chem. Soc. 1976, 98, 2868-2877.
27. b) Evans, D. A. In Asymmetric Synthesis; Vol. 3, Morrison, J. D. Ed,; Academic Press: Orlando, 1984; pp. 1-110.
28. Detailed examinations on lithium-hydrogen interchange between lithium dialkylamides and secondary amines in solution are reported. Fraser, R. R.; Baignée, A.; Bresse, M.; Hata, K. Tetrahedron Lett. 1982, 23, 4195-4198.
29. For example, pKa values of the conjugate acids of ethylamine and trifluoroethylamine are reported to be 10.97 and 5.84, respectively. Jencks, W. P.; Gilchrist, M. J. Am. Chem. Soc. 1968, 90, 2622-2637.
30. 18.
31. In the present paper, the reaction conditions using 1.2 equivalents of (R)-2b are called stoichiometric conditions, while those using a combination of 0.3 equivalent (or less) of (R)-2b∼e in the presence of excess 5a∼h are called catalytic conditions.
32. Since we have no data on the relative rates of deprotonation vs. lithium-hydrogen interchange, it is not possible to explain this difference at present.
33. a) Shirai, R.; Aoki, K.; Sato, D.; Kim, H.-D.; Murakata, M.; Yasukata, T.; Koga, K. Chem. Pharm. Bull. 1994, 42, 690-693.
34. b) Hoover, J. R. Diss. Abstr. Univ. Oklahoma (Chem. Abstr. 1977, 86, 132704t.
35. c) Najer, H.; Giudicelli, R.; Sette, J. Bull. Soc. Chim. Fr. 556-559 (1962).
36. d) Sacco, Jr., L. J.; Anthony, P. Z.; Borgen, D. R.; Ginger, L. G.; J. Am. Chem. Soc. 1954, 76, 303-305.
37. e) Ger. Pat. 823451 (Chem. Abstr. 1955, 49, 3272b.)
38. Aoki, K.; Nakajima, M.; Tomioka, K.; Koga, K. Chem. Pharm. Bull. 1993, 41, 994-996.
39. Gadekar, S. M.; Nibi, S.; Cohen, E. J. Med. Chem. 1868, 11, 811-814.
40. Robertson, J. E.; Biel, J. H.; DiPierro, F. J. Med. Chem. 1963, 6, 381-384.
41. Shioiri, T.; Yokoyama, Y.; Kasai, Y.; Yamada, S. Tetrahedron 1976, 32, 2211-2217.
42. 25 +180 (benzene).