A mild and chemoselective method for the reduction of conjugated isoxazolines to beta-hydroxy ketones

J W Bode; E M Carreira

doi:10.1021/ol015885d

A mild and chemoselective method for the reduction of conjugated isoxazolines to beta-hydroxy ketones

Org Lett. 2001 May 17;3(10):1587-90. doi: 10.1021/ol015885d.

Authors

J W Bode¹, E M Carreira

Affiliation

¹ Laboratorium für Organische Chemie, ETH-Zentrum, Universitätstrasse 16, CH-8092 Zürich, Switzerland.

PMID: 11388873
DOI: 10.1021/ol015885d

Abstract

A new procedure for the selective reduction of conjugated Delta(2)-isoxazolines to the corresponding unsaturated beta-hydroxy ketones is described. The use of SmI(2) as the reducing agent and B(OH)(3) to hydrolyze the resulting imine results in a mild, convenient, and chemoselective protocol for this otherwise difficult transformation and complements existing methodology for the preparation of beta-hydroxy ketones via nitrile oxides.