Enantioselective and Catalytic Method for α-Crotylation of Aldehydes with a Kinetic Self-Refinement of Stereochemistry

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Abstract

Kinetic refinery: A practical, highly stereoselective, two-step catalytic protocol for the α-allylation of aldehydes, starting from crotyltrichlorosilanes, has been developed (see scheme). In each reaction step, one of the stereoisomers reacted faster than the other, which resulted in a kinetic stereochemical (E/Z) self-refinement of the system and led to the formation of virtually enantiomerically and geometrically pure linear homoallylic alcohols in high yield.

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