NaIO4/LiBr-mediated Diastereoselective Dihydroxylation of Olefins:  A Catalytic Approach to the Prevost−Woodward Reaction

Lourdusamy Emmanuvel, Tanveer Mahammad Ali Shaikh, and Arumugam Sudalai*
Chemical Engineering and Process Development Division, National Chemical Laboratory, Pashan Road, Pune 411008, India
Org. Lett., 2005, 7 (22), pp 5071–5074
DOI: 10.1021/ol052080n
Publication Date (Web): September 30, 2005
Copyright © 2005 American Chemical Society
*

 Corresponding author. Phone:  +91-020-25902174. Fax:  +91-20-25893359.

, a.sudalai@ncl.res.in

Abstract

Abstract Image

LiBr catalyzes efficiently the dihydroxylation of alkenes to afford syn and anti diols with excellent diastereoselectivity depending upon the use of NaIO4 (30 mol %) or PhI(OAc)2 (1 equiv), respectively, as the oxidants. The oxidation of non-benzylic halides has been achieved for the first time to afford the corresponding diols in excellent yields.

Tools

History

  • Published In Issue October 27, 2005
  • Received August 29, 2005

Recommend & Share

Related Content

Other ACS content by these authors: