Regioselective Tandem N-Alkylation/C-Acylation of β,γ-Alkynyl α-Imino Esters

被引：54
|
作者：
Mizota, Isao [1 ]
Matsuda, Yuri [1 ]
Kamimura, Satoshi [1 ]
Tanaka, Hirotaka [1 ]
Shimizu, Makoto [1 ]
机构：
[1] Mie Univ, Dept Chem Mat, Grad Sch Engn, Tsu, Mie 5148507, Japan
来源：
ORGANIC LETTERS | 2013年 / 15卷 / 16期
关键词：
CARBOXYLIC-ACID DERIVATIVES; ACYLIUM ION FORMATION; BETA-ALKYNYL ESTERS; AMINO-ACIDS; ELECTROPHILIC AMINATION; 3-COMPONENT REACTION; GRIGNARD-REAGENTS; FACILE SYNTHESIS; ALLENYL ESTERS; ALDOL REACTION;
D O I：
10.1021/ol401934x
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new synthesis of alpha-quaternary alkynyl amino esters and allenoates was developed utilizing umpolung N-addition to beta,gamma-alkynyl alpha-imino esters followed by regioselective acylation. The reaction exhibits broad substrate generality and unique regioselectivity. Moreover, synthesis of alpha-quaternary alkynyl amino esters was also carried out via oxidation of the intermediary enolate followed by alkylation.
引用
收藏
页码：4206 / 4209
页数：4
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