DIISOPROPYL TARTRATE-MODIFIED (E)-GAMMA-[(MENTHOFURYL)DIMETHYLSILYL]ALLYLBORONATE, AN IMPROVED CHIRAL REAGENT FOR THE ANTI-ALPHA-HYDROXYALLYLATION OF ALDEHYDES - APPLICATION TO THE ENANTIOSELECTIVE SYNTHESIS OF (-)-SWAINSONINE

被引：30

作者：

HUNT, JA ^{[1
]}

ROUSH, WR ^{[1
]}

机构：

[1] INDIANA UNIV,DEPT CHEM,BLOOMINGTON,IN 47405

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 04期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/0040-4039(94)02295-M

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An enantioselective synthesis of anti 1,2-diols via the reactions of aldehydes and the tartrate ester-modified (E)-gamma-(menthofurylsilyl)allylboronate 5 has been developed. This methodology is applied to a brief, enantioselective synthesis of (-)-swainsonine.

引用

页码：501 / 504

页数：4

共 36 条

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[26] A STEREOCHEMICALLY GENERAL-SYNTHESIS OF 2-DEOXYHEXOSES VIA THE ASYMMETRIC ALLYLBORATION OF 2,3-EPOXYALDEHYDES
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[27] ASYMMETRIC-SYNTHESIS USING DIISOPROPYL TARTRATE MODIFIED (E)-CROTYLBORONATES AND (Z)-CROTYLBORONATES - PREPARATION OF THE CHIRAL CROTYLBORONATES AND REACTIONS WITH ACHIRAL ALDEHYDES
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[28] ASYMMETRIC-SYNTHESIS USING TARTRATE ESTER MODIFIED ALLYLBORONATES .1. FACTORS INFLUENCING STEREOSELECTIVITY
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