Substrate Binding in the Asymmetric Dihydroxylation Reaction − Investigation of the Stereoselectivity in the Dihydroxylation ofCs-Symmetric Divinylcarbinol Derivatives

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The mechanism of the asymmetric dihydroxylation (AD) reaction has been hotly disputed. We have studied the stereochemical outcome of the AD reaction on a series of Cs-symmetric divinylcarbinol derivatives in order to shed light on the binding mode of the substrate to the osmium tetroxide−ligand complex. The product distribution is dependent on the size of the allylic substituent, and on the type and class of ligand. It is postulated that the diastereospecificity of the reactions originates from attractive forces between the substrate and the ligand. These interactions are independent of the interactions responsible for the enantioselectivity in the AD reaction.