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A Convenient Method for Dihydroxylation of Olefins by the Combined Use of Osmium Tetroxide and Dihydroxyphenyiborane

Iwasawa Nobuharu, Kato Takashi, Narasaka Koichi*

*Department of Chemistry, Faculty of Science, The University of Tokyo

I. Nobuharu, K. Takashi, N. Koichi, Chem. Lett., 1988, 1721-1724.

DOI: 10.1021/jo000191o (free Supporting Information)


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Abstract

cis-Dihydroxylation of olefins with a catalytic amount of osmium tetroxide and N-methylmorpholine N-oxide proceeds smoothly in an organic solvent in the presence of dihydroxyphenylborane to give the corresponding phenylboronic esters in good yields. The use of a diol captor prevents further oxidation of the products and makes the isolation procedure easier.

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Key Words

Upjohn Dihydroxylation, NMO


ID: J42-Y2000