Stereochemically divergent pathways for the allylation and crotylation reactions of anti- and syn-β-hydroxy-α-methyl aldehydes with allyl- and crotyltrifluorosilanes

被引：9

作者：

Chemler, SR

Roush, WR ^{[1
]}

机构：

[1] Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA

[2] Indiana Univ, Dept Chem, Bloomington, IN 47405 USA

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 25期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/S0040-4039(99)00730-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Allylation and crotylation reactions of 2,3-anti-beta-hydroxy-alpha-methyl aldehydes 10 and 11 with allyl and crotyltrifluorosilanes 2, 8 and 9 proceed with high selectivity via the bicyclic chelated transition states 3 and 30. In contrast, analogous allylation and crotylation reactions of the 2,3-syn-beta-hydroxy-alpha-methyl aldehydes 12 and 13 with 2, 8 and 9 are generally less selective and proceed preferentially by way of the normal Zimmerman-Traxler transition states 6 and 32. (C) 1999 Elsevier Science Ltd. All rights reserved.

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页码：4643 / 4647

页数：5

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