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

页码：4206 / 4209

页数：4

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