ASYMMETRIC DIHYDROXYLATION OF ACROLEIN ACETALS - SYNTHESIS OF STABLE EQUIVALENTS OF ENANTIOPURE GLYCERALDEHYDE AND GLYCIDALDEHYDE

被引:24
作者
OI, R [1 ]
SHARPLESS, KB [1 ]
机构
[1] Scripps Res Inst, DEPT CHEM, LA JOLLA, CA 92037 USA
关键词
D O I
10.1016/0040-4039(92)88149-Y
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Asymmetric dihydroxylation (ADH) of acrolein acetals afforded optically active glyceraldehyde equivalents. Enantiopure 3-(1,2-dihydroxyethyl)-1,5-dihydro-3H-2,4-benzodioxepine 3, a protected glyceraldehyde, was obtained from the corresponding acrolein acetal 2 by ADH and subsequent recrystallization. Enantiopure 3-(1,2-epoxyethyl)-1,5-dihydro-3H-2,4-benzodioxepine 5, a protected glycidaldehyde, was produced in two steps from 3.
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页码:2095 / 2098
页数:4
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