Highly stereoselective metathesis reaction between optically active hydrosilane and copper(I) salt in 1,3-dimethyl-2-imidazolidinone

被引：26

作者：

Ito, H ^{[1
]}

Ishizuka, T ^{[1
]}

Okumura, T ^{[1
]}

Yamanaka, H ^{[1
]}

Tateiwa, J ^{[1
]}

Sonoda, M ^{[1
]}

Hosomi, A ^{[1
]}

机构：

[1] Univ Tsukuba, Dept Chem, Ibaraki, Osaka 3058571, Japan

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 1999年 / 574卷 / 01期

关键词：

stereoselective metathesis; optically active; hydrosilane;

D O I：

10.1016/S0022-328X(98)00923-1

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Highly stereoselective metathesis reactions between optically active silyl compounds and copper(I) salts in 1,3-dimethyl-2-imidazolidinone (DMI) are reported. The substitution reaction of (+)-alpha-naphthylphenylmethylsilane with a mixture of lithium tert-butoxide and copper(I) salt smoothly proceeded in DMI to give the corresponding silyl ether with a high degree of retention of the configuration in a quantitative yield. The use of DMI as a solvent and the presence of a chloride ion are necessary for this reaction. An optically active alkynylsilane also reacted with the mixed reagent to afford the corresponding silyl ether. A mechanism of oxidative addition of the hydrosilane and reductive elimination of the silyl ether on copper is proposed. (C) 1999 Elsevier Science S.A. All rights reserved.

引用

页码：102 / 106

页数：5

共 17 条

[1] THE COPPER CATALYZED REACTION OF SODIUM METHOXIDE WITH ARYL BROMIDES - A MECHANISTIC STUDY LEADING TO A FACILE SYNTHESIS OF ANISOLE DERIVATIVES [J].