Yeast-mediated synthesis of optically active diols with C-2-symmetry and (R)-4-pentanolide

被引:49
作者
Ikeda, H [1 ]
Sato, E [1 ]
Sugai, T [1 ]
Ohta, H [1 ]
机构
[1] KEIO UNIV,DEPT CHEM,YOKOHAMA,KANAGAWA 223,JAPAN
关键词
D O I
10.1016/0040-4020(96)00373-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reduction of some diketones and a ketoacid with yeast, Pichia farinosa IAM 4682 was examined. The reduction of carbonyl groups proceeded highly selectively with an anti-Prelog fashion to give (R)-alcohols. (2R,5R)-2,5-Hexanediol (83% yd., >99% e.e., 95% d.e.), (2R,4R)-2,4-pentanediol (94% yd., >99% e.e., 98% d.e.), and (R)-4-pentanolide (67% yd., >99% e.e.) were highly efficiently obtained from the corresponding ketones. Effect of the structure of substrate on the stereochemical course as well as the selectivity were discussed. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:8113 / 8122
页数:10
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