Highly Regio- and Stereoselective Heck Reaction of Allylic Esters with Arenediazonium Salts: Application to the Synthesis of Kavalactones

被引：59

作者：

Moro, Angelica Venturini ^{[1
]}

Pereira Cardoso, Flavio Sega ^{[1
]}

Duarte Correia, Carlos Roque ^{[1
]}

机构：

[1] Univ Estadual Campinas, Inst Quim, UNICAMP, BR-13084971 Sao Paulo, Brazil

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 16期

基金：

巴西圣保罗研究基金会;

关键词：

PALLADIUM-CATALYZED ARYLATION; DIAZONIUM SALTS; IONIC LIQUIDS; METHYL-ESTER; ARYL IODIDES; KAVA-KAVA; ALCOHOLS; EFFICIENT; PD(OAC)(2); COMPLEX;

D O I：

10.1021/ol901416e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly efficient palladium-catalyzed Heck reaction of allylic esters with arenediazonium salts is described. The reaction proceeds under mild conditions, with excellent to total regio- and stereochemical control and with retention of the traditional leaving group. Furthermore, the generality of the present methodology is illustrated by the short total synthesis of the natural kavalactones, yangonine, (+/-)-methysticin, and (+/-)-dihydromethysticin.

引用

页码：3642 / 3645

页数：4

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