New cyclic zwitterionic building blocks for the synthesis of piperidine-2,4-dione and pyridine-2-one compounds

被引：14

作者：

Palillero, Angel ^{[1
]}

Teran, Joel L. ^{[1
]}

Gnecco, Dino ^{[1
]}

Juarez, Jorge R. ^{[1
]}

Orea, Maria L. ^{[1
]}

Castro, Alejandro ^{[1
]}

机构：

[1] Benemerita Univ Autonoma Puebla, Ctr Quim, Puebla 72570, Mexico

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 29期

基金：

芬兰科学院;

关键词：

ASYMMETRIC-SYNTHESIS; SULFUR YLIDES; ENANTIOSELECTIVE SYNTHESIS; CHIRAL AUXILIARY; DERIVATIVES; EPOXIDATION; EPOXIDES; MEDIATOR; SULFIDE; SCOPE;

D O I：

10.1016/j.tetlet.2009.02.143

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In this Letter we describe the synthesis of new chiral cyclic zwitterionic pyridin-2-one compounds 5a,b via an intramolecular ring-closure reaction of a stabilize amide sulfur ylide 4a,b derived from (R)-(-)-2-phenylglycinol and (R)-(+)-phenylethylamine in a high yield. In addition, we proved the utility of 5a,b to produce piperidine-2,4-dione 6a,b and pyridine-2-one 7a,b depending on the reaction conditions. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：4208 / 4211

页数：4

共 3 条

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