Double nucleophilic N-alkylation of α-oxime-esters with Grignard reagents

被引：17

作者：

Mizutani, Yusuke ^{[1
]}

Tanimoto, Hiroki ^{[1
]}

Morimoto, Tsumoru ^{[1
]}

Nishiyama, Yasuhiro ^{[1
]}

Kakiuchi, Kiyomi ^{[1
]}

机构：

[1] Nara Inst Sci & Technol, NAIST, Grad Sch Mat Sci, Ikoma Nara 6300192, Japan

来源：

TETRAHEDRON LETTERS | 2012年 / 53卷 / 44期

关键词：

Umpolung; Amino acid; Electrophilic amination; Cascade reaction; Oxime; PRIMARY AMINES; UMPOLUNG; BENZOPHENONE; IMINOESTERS; DERIVATIVES; REACTIVITY; ADDITIONS; CHLORIDE; KETONES; IMINES;

D O I：

10.1016/j.tetlet.2012.08.091

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Double nucleophilic N-alkylation of alpha-oxime-esters, affording N,N-dialkyl-alpha-amino acids is herein described. Grignard reagents accomplished double N-alkylations via umpolung and various N.N-dialkylated alpha-amino acids were successfully synthesized in 15 min. Both electron-withdrawing sulfonyl groups and electron-donating silyl and methyl groups on oximes were available. Alkylmagnesium species and (E)-configuration of alpha-oxime-ester were essential to this cascade reaction. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：5903 / 5906

页数：4

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