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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, Email: a.sudalaincl.res.in

L. Emmanuvel, T. M. A. Shaikh, A. Sudalai, Org. Lett., 2005, 7, 5071-5074.

DOI: 10.1021/ol052080n (free Supporting Information)


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Abstract

LiBr is an efficient catalyst for the dihydroxylation of alkenes to afford either syn or anti diols with excellent diastereoselectivity depending upon the use of NaIO4 or PhI(OAc)2 as the oxidants.

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Key Words

1,2-diols, Prévost Reaction, Woodward Reaction, Sodium periodate, Hypervalent iodine compounds


ID: J54-Y2005-1800