β,γ-炔基-α-亚氨基酯的区域选择性串联 N-烷基化/C-酰化反应。

Regioselective tandem N-alkylation/C-acylation of β,γ-alkynyl α-imino esters.

机构信息

Department of Chemistry for Materials, Graduate School of Engineering, Mie University, Tsu, Mie 514-8507, Japan.

出版信息

Org Lett. 2013 Aug 16;15(16):4206-9. doi: 10.1021/ol401934x. Epub 2013 Aug 2.

DOI:10.1021/ol401934x

Abstract

A new synthesis of α-quaternary alkynyl amino esters and allenoates was developed utilizing umpolung N-addition to β,γ-alkynyl α-imino esters followed by regioselective acylation. The reaction exhibits broad substrate generality and unique regioselectivity. Moreover, synthesis of α-quaternary alkynyl amino esters was also carried out via oxidation of the intermediary enolate followed by alkylation.

摘要

开发了一种新的α-季碳炔基氨基酯和丙二烯酸酯的合成方法，利用β，γ-炔基α-亚胺酯的反转 N-加成，然后进行区域选择性酰化。该反应具有广泛的底物通用性和独特的区域选择性。此外，还通过中间体烯醇化物的氧化，然后进行烷基化反应，实现了α-季碳炔基氨基酯的合成。