An approach to catalytic asymmetric deprotonation of 4-substituted cyclohexanones

Tetrahedron Letters

Volumn 37, Issue 45, 1996, Pages 8195-8198

  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

CYCLOHEXANE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030569392     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01859-X     Document Type: Article

References (19)

1. 1. (a) Koga, K. J. Synth. Org. Chem., Jpn. 1990, 48, 463-475.
2. (b) Cox, P. J.; Simpkins, N. S. Tetrahedron: Asymmetry 1991, 2, 1-26.
3. (c) Koga, K. Pure & Applied Chem. 1994, 66, 1487-1492.
4. (d) Koga, K.; Shindo, M. J. Synth. Org. Chem., Jpn. 1995, 53, 1021-1032.
5. 2. (a) Shirai, R.; Tanaka, M.; Koga, K. J. Am. Chem. Soc. 1986, 108, 543-545.
6. (b) Sato, D.; Kawasaki, H.; Shimada, I.; Arata, Y.; Okamura, K.; Date, T.; Koga, K. J. Am. Chem. Soc. 1992, 114, 761-763.
7. (c) Aoki, K.; Nakajima, M.; Tomioka, K.; Koga, K. Chem. Pharm. Bull. 1993, 41, 994-996.
8. (d) Aoki, K.; Noguchi, H.; Tomioka, K.; Koga, K. Tetrahedron Lett., 1993, 34, 5105-5108.
9. 6LiCl (0 ppm) in methanol as a reference) as a doublet of triplets (J=7, 1.2, and 1.2 Hz).
10. 15N-aniline (52.0 ppm) in THF as a reference) as a triplet (J=1.2 Hz), a triplet (J=7 Hz), and a triplet (7=1.2 Hz), respectively.
11. 4. Ireland, R. E.; Mueller, R. H.; Willard, A. K. J. Am. Chem. Soc. 1976, 98, 2868-2877.
12. 5. Hydrogen-lithium interchange between lithium amides and secondary amines is reported: Fraser, R. R.; Baignée, A.; Bresse, M.; Hata, K. Tetrahedron Lett. 1982, 23, 4195-4198.
13. 6. Benzylic proton signals of (R)-4a, (R)-4b, (R)-5a, and (R)-5b appear at ca. 4.2, ca. 4.3, ca. 3.7, and ca. 3.95 ppm, respectively, as a doublet-like quartet. Tridentate achiral lithium amide (8) and its corresponding amine (7) have no signals in this region.
14. 18.
15. 8. Corey, E. J.; Gross, A. W. Tetrahedron Lett. 1984, 25, 495-498.
16. 9 For details, see footnote 7 in ref. 2d.
17. 2c
18. 11. The reasons are not yet clear and are under investigation.
19. 12. An example of catalytic asymmetric deprotonation of meso-epoxides is reported: Asami, M.; Ishizaki, T.; Inoue, S. Tetrahedron: Asymmetry 1994, 5, 793-796.