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
收藏
页码：5903 / 5906
页数：4
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