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

Authors
Bode, JW Carreira, EM
Citation
Jw. Bode et Em. Carreira, A mild and chemoselective method for the reduction of conjugated isoxazolines to beta-hydroxy ketones, ORG LETT, 3(10), 2001, pp. 1587-1590
Citations number
14
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
10
Year of publication
2001
Pages
1587 - 1590
Database
ISI
SICI code
1523-7060(20010517)3:10<1587:AMACMF>2.0.ZU;2-3
Abstract
A new procedure for the selective reduction of conjugated Delta (2)-isoxazo lines to the corresponding unsaturated beta -hydroxy ketones is described. The use of SmI2 as the reducing agent and B(OH)(3) to hydrolyze the resulti ng imine results in a mild, convenient, and chemoselective protocol for thi s otherwise difficult transformation and complements existing methodology f or the preparation of beta -hydroxy ketones via nitrile oxides.