DIASTEREOSELECTIVE ALDOL REACTIONS OF CHIRAL ALDEHYDES AND CHIRAL METHYL KETONES - DEPENDENCE OF STEREOSELECTIVITY ON THE METAL ENOLATE, THE ALDEHYDE 2,3-STEREOCHEMISTRY, AND THE ALDEHYDE BETA-ALKOXY PROTECTING GROUP

被引：40

作者：

GUSTIN, DJ ^{[1
]}

VANNIEUWENHZE, MS ^{[1
]}

ROUSH, WR ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 20期

关键词：

D O I：

10.1016/0040-4039(95)00626-N

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stereoselectivity of aldol reactions of chiral aldehydes 5 and 11 with methyl ketone enolates is highly dependent on the aldehyde 2,3-stereochemistry, the aldehyde beta-alkoxy protecting group, and the metal enolate. The selectivity trends are rationalized by a competition between chair-like and boat-like transition states.

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页码：3443 / 3446

页数：4

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