Asymmetric alkyldifluoroboranes and their use in secondary amine synthesis

被引：105

作者：

Matteson, DS ^{[1
]}

Kim, GY ^{[1
]}

机构：

[1] Washington State Univ, Dept Chem, Pullman, WA 99164 USA

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 13期

关键词：

D O I：

10.1021/ol025973d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Asymmetric diol boronic esters with potassium bifluoride form the corresponding alkyltrifluoroborate and free diol under mild conditions. Defluoridation with tetrachlorosilane produces an alkyldifluoroborane intermediate. This conversion of relatively unreactive boronic esters to derivatives that are strong Lewis acids opens new synthetic opportunities, as illustrated by the preparation of (R)-2-phenylpyrrolidine in 98% ee from a pinanediol or 1,2-dicyclohexyl-1,2-ethanediol boronic ester via potassium (2-phenyl-4-azidobutyl)trifluoroborate.

引用

页码：2153 / 2155

页数：3

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