Rearrangement of epoxynitriles: A convenient homologation of acyclic and cyclic ketones to carboxylic acids

被引：9

作者：

Badham, NF

Mendelson, WL

Allen, A

Diederich, AM

Eggleston, DS

Filan, JJ

Freyer, AJ

Killmer, LB

Kowalski, CJ

Liu, L

Novack, VJ

Vogt, FG

Webb, KS

Yang, J

机构：

[1] GlaxoSmithKline Pharmaceut, Dept Synthet Chem, King Of Prussia, PA 19406 USA

[2] GlaxoSmithKline Pharmaceut, Dept Analyt Chem, King Of Prussia, PA 19406 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 15期

关键词：

Carboxylic acids - Lithium compounds - Nitrile resins - Reaction kinetics;

D O I：

10.1021/jo025737g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convenient two-step homologation of both aliphatic and aromatic ketones to the corresponding carboxylic acid has been developed. First ketones were converted to epoxynitriles with the Darzens reaction. Second, a Lewis acid mediated rearrangement of these epoxynitriles with lithium bromide was achieved to give homologated secondary alkanoic acids (as well as aryl-alkanoic) in good yields. The mechanism and the scope of the rearrangement reaction were investigated. This strategy constitutes a two-step homologation of ketones to secondary carboxylic acids.

引用

页码：5440 / 5443

页数：4

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