Controlled reduction of tertiary amides to the corresponding aldehydes or amines using dialkylboranes

被引：32

作者：

Godjoian, G ^{[1
]}

Singaram, B ^{[1
]}

机构：

[1] UNIV CALIF SANTA CRUZ,DEPT CHEM & BIOCHEM,SANTA CRUZ,CA 95064

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 10期

关键词：

D O I：

10.1016/S0040-4039(97)00179-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Several tertiary amides were reduced using one or two equivalents of various dialkylboranes, such as 9-borabicyclo[3.3.1] nonane (9-BBN), dicyclohexylborane (Chx(2)BH), or dislamylborane (Sia(2)BH). The reduction of tertiary amides having alkyl substituents of varying steric requirement at the nitrogen atom, required two equivalents of 9-BBN for complete reduction and gave the corresponding tertiary amines. However, sterically more hindered dialkylboranes such as Chx(2)BH and Sia(2)BH, reacted in 1:1 stoichiometry with tertiary amides and partially reduced them to the corresponding aldehydes. (C) 1997 Elsevier Science Ltd.

引用

页码：1717 / 1720

页数：4

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