Tetrahedron letters

The directed dihydroxylation of allylic alcohols

TJ Donohoe, PR Moore, MJ Waring, NJ Newcombe

Index: Donohoe, Timothy J.; Moore, Peter R.; Waring, Michael J.; Newcombe, Nicholas J. Tetrahedron Letters, 1997 , vol. 38, # 28 p. 5027 - 5030

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Citation Number: 95

Abstract

The preparation and dihydroxylation of a series of polyenes and cyclic allylic alcohols using the TMEDA/osmium tetroxide mixture is reported. Remarkably, these reagents lead to high levels of regiochemical and stereochemical control as the oxidant hydrogen-bonds to the allylic alcohol group. A mechanistic hypothesis is presented which invokes the formation of a reactive, bidentate complex between osmium tetroxide and TMEDA at low temperatures.

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