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一种高效构建螺环缩酮、单不饱和螺环缩酮和呋喃的方法:Hg(II)催化的炔二醇和三醇的环化反应。

A highly efficient access to spiroketals, mono-unsaturated spiroketals, and furans: Hg(II)-catalyzed cyclization of alkyne diols and triols.

机构信息

Département de chimie, Faculté des sciences et de génie, Pavillon Alexandre-Vachon, Université Laval, 1045, avenue de la Médecine, Québec (Québec) G1 V 0A6, Canada.

出版信息

Org Lett. 2011 Jun 17;13(12):3178-81. doi: 10.1021/ol201102x. Epub 2011 May 23.

Abstract

Hg(II) salts are identified as highly efficient catalysts for the versatile construction of spiroketals from alkyne diols in aqueous conditions. Monounsaturated spiroketals and furans were accessed with equal ease when propargylic triols (or propargylic diols) were subjected to similar conditions. Even the semiprotected alkyne diols gave the corresponding spiroketals with the same ease in a cascade manner. The reactions are instant and high yielding at ambient temperatures. Regioselectivity issues are well addressed.

摘要

Hg(II) 盐被鉴定为在水相条件下从炔二醇中高效构建螺缩酮的高效催化剂。当丙炔三醇(或丙炔二醇)在类似条件下反应时,可轻松获得单不饱和螺缩酮和呋喃。即使是半保护的炔二醇也能以级联方式以相同的简便方式得到相应的螺缩酮。反应在环境温度下即时进行且产率高。区域选择性问题得到了很好的解决。

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