CHEMISTRY OF ORGANOSILICON COMPOUNDS .259. HIGHLY STEREOSELECTIVE ALLYLATION OF ALDEHYDES WITH PENTACOORDINATE ALLYLSILICATES IN HYDROXYLIC MEDIA - DISCRIMINATION BETWEEN LINEAR AND ALPHA-BRANCHED ALKANALS

被引：59

作者：

KIRA, M

SATO, K

SAKURAI, H

机构：

[1] The Department of Chemistry, Faculty of Science, Tohoku University, Aoba-ku

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1990年 / 112卷 / 01期

关键词：

D O I：

10.1021/ja00157a040

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Allylation of aldehydes with allyltrifluorosilanes in the presence of a wide variety of hydroxy compounds and triethylamine gave the corresponding homoallyl alcohols in regio- and stereospecific manner. Pentacoordinate allylsilicates are suggested as intermediates. The present reagent system can discriminate linear from α-branched alkanals. The structure and reactivity relationship in pentacoordinate allylsilicates is discussed in terms of Lewis acidity of the central silicon. © 1990, American Chemical Society. All rights reserved.

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页码：257 / 260

页数：4

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