A novel synthesis of β-ketosilanes via organoboranes

被引：7

作者：

Bhat, NG ^{[1
]}

Martinez, C ^{[1
]}

De los Santos, J ^{[1
]}

机构：

[1] Univ Texas Pan Amer, Dept Chem, Edinburg, TX 78539 USA

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 34期

关键词：

trimethylsilylmethyllithium; beta-ketosilanes; nucleophilic substitution; organoboranes; 1-bromo-1-alkynes;

D O I：

10.1016/S0040-4039(00)01088-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convenient, novel synthesis of beta-ketosilanes based on (Z)-1-bromo-1-alkenylboronate esters is developed. alpha-Bromo-(Z)-1-alkenylboronate esters readily available using literature procedures smoothly undergo a reaction with trimethylsilylmethyllithium in tetrahydrofuran to provide the corresponding 'ate' complexes. These 'ate' complexes will undergo intramolecular nucleophilic substitution reactions to afford the corresponding (E)-trisubstituted olefins containing trimethylsilylmethyl moiety. The oxidation of these intermediates with sodium acetate and hydrogen peroxide provides beta-ketosilanes in good yields (63-75% yield). (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：6541 / 6544

页数：4

共 18 条

[11] HOMOLOGATION OF BORONIC ESTERS TO ALPHA-CHLORO BORONIC ESTERS [J].