The highly enantioselective borane reduction of ketones catalyzed by chiral oxazaborolidine derived from sterically constrained amino alcohols

Heterocycles

Volumn 46, Issue 1, 1997, Pages 189-192

  Hashimoto, Noriaki ^a   Ishizuka, Tadao ^a   Kunieda, Takehisa ^a  

^a KUMAMOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000810136     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-97-s73     Document Type: Article

References (13)

1. For recent reviews, see : a) L. Deloux and M. Srebnik, Chem. Rev., 1993, 93, 763.
2. b) S. Wallbaum and J. Martens, Tetrahedron : Asymmetry, 1992, 3, 1475.
3. c) V. K. Singh, Synthesis. 1992, 605.
4. S. Ituno, Y. Sakurai, K. Ito, A. Hirao, and S. Nakahama, Bull. Chem. Soc. Jpn., 1987, 60, 395 and references therein.
5. E. J. Corey, S. Shibata, and R. K. Bakshi, J. Org. Chem., 1988, 53, 2861 and references therein.
6. a) M. Masui and T. Shioiri, Synlett, 1996, 49 and 273.
7. b) Y. Hong, Y. Gao, X. Nie, and M. C. Zepp, Tetrahedron Lett., 1994, 35, 6631.
8. N. Hashimoto, T. Ishizuka, and T. Kunieda, Tetrahedron Lett., 1994, 35, 721.
9. H. Matsunaga, K. Kimura, T. Ishizuka, M. Haratake,and T. Kunieda, Tetrahedron Lett., 1991, 32, 7715.
10. 3,) δ: 7.33-7.11 (m, 8H), 4.75 (dd, J=7.9, 3.7 Hz, 1H), 4.50 (d, 1H, J=3.7 Hz), 4.17 (d, J=2.5 Hz), 3.93 (dd, J=7.9, 2.5 Hz, 1H), 2.34 (br s, 1H), -0.23 (s, 3H)
11. 3-THF complex (2.0 mmol) in THF (20 mL) at 0 °C via a syringe pump over a period of 90 min and the mixture was then acidified with 2 N HC1. The usual work-up, followed by Chromatographie purification, gave the chiral alcohol. b) In the above procedure, the amino alcohol was used in the place of the oxazaborolidine.
12. a) D. K. Jones, D. C. Liotta, I. Shinkai, and D. J. Mathre, 7. Org. Client., 1993, 55, 799.
13. b) G. J. Quallich, J. F. Blake, and T. M. Woodall,7. Am. Chem. Soc., 1994, 116, 8516.