1,1'-binaphthalene-8,8'-diol as en efficient chiral controller: Highly enantioselective synthesis of optically active ketones

Tetrahedron Letters

Volumn 37, Issue 41, 1996, Pages 7373-7376

  Fuji, Kaoru ^a   Yang, Xiao Shen ^a   Tanaka, Kiyoshi ^a   Asakawa, Naoyuki ^a   Hao, Xiao Jian ^b  

^a KYOTO UNIVERSITY   (Japan)

^b KUNMING INSTITUTE OF BOTANY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

KETONE;

ARTICLE; CHIRALITY; DRUG PURIFICATION; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030573980     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01659-0     Document Type: Article

References (15)

1. (1) For a review of the catalytic reactions, see: Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994.
2. (2) For a review of the stoichiometric reactions, see: Rosini, C.; Franzini, L.; Raffaelli, A.; Salvatori, P. synthesis 1992, 503.
3. (3) Artz, S. P.; de Grandpre, M. P.; Cram. D. J. J. Org. Chem. 1985, 50, 1486.
4. 3
5. (b) Fuji, K.; Kawabata, T.; Kuroda, A.; Taga, T. J. Org. Chem. 1995, 60, 1914.
6. (c) Fukushi, Y.; Shigematsu, K.; Mizutani, J.; Tahara, S. Tetrahedron Lett. 1996, 32, 4737.
7. (5) (a) Tanaka, F.; Node, M.; Tanaka, K.; Mizuchi, M.; Hosoi, S.; Nakayama, M.; Taga, T.; Fuji, K. J. Am. Chem. Soc. 1995, 117, 12159.
8. (b) Fuji, K.; Tanaka, K.; Mizuchi, M.; Hosoi, S. Tetrahedron Lett. 1991, 32, 7277.
9. (6) For optical resolution of 2, see: Ref. 4b and Fabbri, D.; Delogu, G.; Lucchi, O. D. J. Org. Chem. 1995, 60, 6599.
10. 25 -5.3 (neat) for the (R)-isomer of 15.6% ee.
11. (8) Hayashi, T.; Yamamoto, K.; Kumada, T. Tetrahedron Lett. 1975, 3.
12. D value was reported. See: van Klaveren, M.; Lambert, F.; Eijkelkamp, J. F. M.; Grove, D. M.; van Koten, G. Tetrahedron Lett. 1994, 35, 6135.
13. (10) Shida, N.; Kabuto, C.; Niwa, T.; Ebata, T.; Yamamoto, Y. J. Org. Chem. 1994, 59, 4068.
14. (11) The MacroModel / AMBER* (version 4.5) force field was used.
15. (12) Ullenius, C.; Christenson, B. Pure Appl. Chem. 1988, 60, 57.