PtCl₂催化的5-烯-1-炔-3-醇体系的环异构化反应。

PtCl2-catalyzed cycloisomerizations of 5-en-1-yn-3-ol systems.

作者信息

Harrak Youssef, Blaszykowski Christophe, Bernard Matthieu, Cariou Kevin, Mainetti Emily, Mouriès Virginie, Dhimane Anne-Lise, Fensterbank Louis, Malacria Max

机构信息

Université Pierre et Marie Curie, Laboratoire de Chimie Organique, UMR CNRS 7611, Tour 44-54, case 229, 4, place Jussieu, 75252 Paris 05, France.

出版信息

J Am Chem Soc. 2004 Jul 21;126(28):8656-7. doi: 10.1021/ja0474695.

DOI:10.1021/ja0474695

PMID:15250710

Abstract

5-En-1-yn-3-ol substrates bearing a free hydroxyl group or an acyl group are highly versatile partners for PtCl2-catalyzed cycloisomerizations. Electrophilic activation of the alkyne moiety triggers at wish a hydride or an O-acyl migration yielding at the end to regioisomeric keto derivatives. The efficient preparation of Sabina ketone, an important monoterpene precursor, has been worked out.

摘要

带有游离羟基或酰基的5-烯-1-炔-3-醇底物是PtCl₂催化的环异构化反应中用途广泛的伙伴。炔烃部分的亲电活化引发了所需的氢化物或O-酰基迁移，最终生成区域异构体酮衍生物。已成功实现了重要单萜前体桧酮的高效制备。