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Stereoselective Synthesis of Tetrasubstituted Olefins through a Halogen-Induced 1,2-Silyl Migration

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  • Colorado State University is acknowledged for the support of our program. Eli Lilly is gratefully acknowledged for a graduate research fellowship to D.A.R.

Abstract

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Migrating through Si valley: The highly stereoselective formation of α-silyl-β- haloenones by way of silicon group migration is described. Electrophilic activation of the alkyne by N-halosuccinimides induced an anti-selective migration to give highly substituted enones (see scheme). These enone products can be readily converted to the all-carbon tetrasubstituted alkenes while maintaining their geometry.

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