钛介导的炔丙醇还原偶联反应立体选择性合成顺式-1,3-二醇。

Diastereoselective synthesis of syn-1,3-diols by titanium-mediated reductive coupling of propargylic alcohols.

机构信息

Depeartment of Chemistry, Texas A&M University, College Station, Texas 77842-3092, USA.

出版信息

Org Lett. 2010 Jan 15;12(2):288-90. doi: 10.1021/ol902609k.

PMID:19961149

Abstract

A titanium-mediated, hydroxy-directed reductive coupling reaction of propargylic alcohols and aldehydes/ketones is described. Excellent diastereoselectivity and synthetically useful yields have been obtained for a range of substrates. This transformation has enabled a highly convergent three-component approach to syn-1,3-diols using (trimethylsilyl)acetylene as a C1 linchpin.

摘要

本文描述了钛介导的、羟基导向的炔丙醇与醛/酮的还原偶联反应。该反应在一系列底物中获得了优异的非对映选择性和具有合成实用性的产率。这种转化为使用(三甲基硅基)乙炔作为 C1 连接基的高立体定向合成 1,3-二醇的三组分方法提供了一种很有前景的途径。