Organic Chemistry Portal

Abstracts

Search:

Regioselective and Stereoselective Cyclizations of Chloropolyols in Water: Rapid Synthesis of Hydroxytetrahydrofurans

Baldip Kang, Stanley Chang, Shannon Decker and Robert Britton*

*Department of Chemistry, Simon Fraser University, Burnaby, British Columbia V5A 1S6, Canada, Email: rbrittonsfu.ca

B. Kang, S. Chang, S. Decker, R. Britton, Org. Lett., 2010, 12, 1716-1719.

DOI: 10.1021/ol100260z


Abstract

A concise, stereoselective synthesis of functionalized tetrahydrofuranols involves heating of readily available chloropolyols in water. These reactions are operationally straightforward and chemoselective for the formation of tetrahydrofurans, obviating the need for complicated protecting group strategies. A short asymmetric synthesis of the natural product (+)-goniothalesdiol is demonstrated.

see article for more examples



Key Words

Tetrahydrofurans, Microwave Synthesis, Green Chemistry


ID: J54-Y2010-1050