Synthesis of α-pyrones via palladium-catalyzed annulation of internal alkynes

被引：70

作者：

Larock, RC ^{[1
]}

Han, XJ ^{[1
]}

Doty, MJ ^{[1
]}

机构：

[1] Iowa State Univ Sci & Technol, Dept Chem, Ames, IA 50011 USA

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 32期

关键词：

palladium and compounds; annulation; halo esters; pyrones;

D O I：

10.1016/S0040-4039(98)01182-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A number of 3,5,6-tri- and 3,4,5,6-tetrasubstituted alpha-pyrones have been prepared in good yields by the reaction of vinylic iodides, bromides or triflates bearing ester functionality with internal alkynes in the presence of a palladium catalyst. The methodology provides an especially simple, convenient, and regioselective route to alpha-pyrones containing aryl, silyl, tert.-alkyl and other hindered groups. The reaction is believed to proceed through a seven-membered palladacyclic salt in which the regiochemistry of the reaction is controlled by steric factors. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：5713 / 5716

页数：4

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