STUDIES ON ORGANOSILICON CHEMISTRY .100. PENTACOORDINATE ALLYLSILICONATES IN ORGANIC-SYNTHESIS - SYNTHESIS OF TRIETHYLAMMONIUM BIS(CATECHOLATO)ALLYLSILICONATES AND SELECTIVE ALLYLATION OF ALDEHYDES

被引：75

作者：

HOSOMI, A ^{[1
]}

KOHRA, S ^{[1
]}

OGATA, K ^{[1
]}

YANAGI, T ^{[1
]}

TOMINAGA, Y ^{[1
]}

机构：

[1] NAGASAKI UNIV,FAC PHARMACEUT SCI,NAGASAKI 852,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 08期

关键词：

D O I：

10.1021/jo00295a033

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Pentacoordinate triethylammonium bis(catecholato)allylsiliconates were synthesized by reaction of allyltrialkoxysilanes, catechol, and triethylamine. The allylsiliconates react with aldehydes without catalyst to give the corresponding homoallyl alcohols in high yields in a completely regiospecific and highly diastereoselective mode. The stereochemistry of the products can be reasonably interpreted by assuming a cyclic six-membered ring transition state. This allylation of aldehydes can also be effected by mixing them with an allyltrialkoxysilane, an alcohol, and an amine, generating the allylsiliconate in situ. © 1990, American Chemical Society. All rights reserved.

引用

页码：2415 / 2420

页数：6

共 70 条

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