Wittig Rearrangement of α-(Propargyloxy)alkyllithiums: Periselectivity and Steric Course at the Lithium-Bearing Terminus

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Abstract
The [2,3]-Wittig rearrangement of an enantiomerically defined α-propargyloxy stannane with butyllithium is shown to proceed with complete inversion of configuration at the Li-bearing terminus. The periselectivity ([2,3]- vs. [1,2]-) of the rearrangement depends markedly upon the nature of substituents on the acetylenic group.

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