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An asymmetric retro-[1,4]-Brook rearrangement of 3-silyl allyloxysilanes has been developed via Si-to-C chirality transfer. Mechanistic studies reveal that the silyl group migrates with retention of configuration. The stereochemical outcome of the newly formed stereogenic carbon center, which has remained a longstanding question, is also clarified, suggesting a diastereoselective Si to C chirality transfer without loss of enantiomeric excess.

Asymmetric retro-[1,4]-Brook rearrangement of 3-silyl allyloxysilanes via chirality transfer from silicon to carbon