DIISOPROPYL TARTRATE (E)-GAMMA-(DIMETHYLPHENYLSILYL)ALLYLBORONATE, A CHIRAL ALLYLIC ALCOHOL BETA-CARBANION EQUIVALENT FOR THE ENANTIOSELECTIVE SYNTHESIS OF 2-BUTENE-1,4-DIOLS FROM ALDEHYDES

被引：44

作者：

ROUSH, WR

GROVER, PT

机构：

[1] Department of Chemistry, Indiana University, Bloomington

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 52期

关键词：

D O I：

10.1016/S0040-4039(00)97300-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An enantioselective synthesis of 4-substituted (E)-2-buten-1,4-diols is described. The method involves the reaction of aldehydes with the chiral PhMe2Si- substituted allylboronate 3 followed by epoxidation (dimethyl dioxirane) and acid catalyzed Petersen rearrangement of the intermediate epoxysilanols.

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页码：7567 / 7570

页数：4

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