STEREOSELECTIVE REDUCTION OF ALPHA,BETA-EPOXY KETONES INTO ERYTHRO-ALPHA,BETA-EPOXY ALCOHOLS WITH SODIUM-BOROHYDRIDE IN THE PRESENCE OF CALCIUM-CHLORIDE

被引:29
作者
FUJII, H [1 ]
OSHIMA, K [1 ]
UTIMOTO, K [1 ]
机构
[1] KYOTO UNIV, FAC ENGN, DEPT IND CHEM, SAKYO KU, KYOTO 60601, JAPAN
关键词
D O I
10.1246/cl.1992.967
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
erythro-alpha,beta-Epoxy alcohols were prepared with high stereoselectivity by sodium borohydride reduction of the corresponding alpha,beta-epoxy ketones in the presence of calcium chloride or manganese(II) chloride regardless of the substituents on the epoxide ring.
引用
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页码:967 / 970
页数:4
相关论文
共 5 条
[1]   ASYMMETRIC INDUCTION AND [2+1] CYCLOADDITIONS .3. DIASTEREOSELECTIVE EPOXIDATIONS OF SECONDARY ALPHA ETHYLENIC ALCOHOLS AND STEREODIRECTED SYNTHESES OF ALPHA EPOXY ALCOHOLS [J].
CHAUTEMPS, P ;
PIERRE, JL .
TETRAHEDRON, 1976, 32 (05) :549-557
[2]   A PRACTICAL AND STEREOSELECTIVE REDUCTION OF 3-KETO-2-METHYL ESTERS OR 3-KETO-2-METHYL AMIDES INTO ERYTHRO-3-HYDROXY-2-METHYL ESTERS OR ERYTHRO-3-HYDROXY-2-METHYL AMIDES WITH NABH4 CATALYZED BY MNCL2 [J].
FUJII, H ;
OSHIMA, K ;
UTIMOTO, K .
TETRAHEDRON LETTERS, 1991, 32 (43) :6147-6150
[3]   HIGHLY STEREOSELECTIVE SYNTHESIS OF ERYTHRO-ALPHA, BETA-EPOXY ALCOHOLS BY THE REDUCTION OF ALPHA, BETA-EPOXY KETONES WITH ZINC BOROHYDRIDE [J].
NAKATA, T ;
TANAKA, T ;
OISHI, T .
TETRAHEDRON LETTERS, 1981, 22 (47) :4723-4726
[4]   AN INTRODUCTION OF CHIRAL CENTERS INTO ACYCLIC SYSTEMS BASED ON STEREOSELECTIVE KETONE REDUCTION [J].
OISHI, T ;
NAKATA, T .
ACCOUNTS OF CHEMICAL RESEARCH, 1984, 17 (09) :338-344
[5]  
PELTER A, 1988, BORANE REAGENTS, P414