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

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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

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ID: J54-Y2005-1800