[2,3]Wittig rearrangement of enantiomerically-defined α-(allyloxy)stannanes: Solid evidence for inversion of configuration at the lithium-bearing migrating terminus

Article abstract of DOI:10.1016/0040-4039(92)89034-A

The [2,3]Wittig rearrangement of enantiomerically-defined α-(allyloxy)stannanes, prepared from (S)-1-tributylstannyl-1-propanol, with butyllithium is shown to proceed with essentially complete inversion of configuration at the lithium-bearing migrating terminus. This inversion stereochemistry is further confirmed by the rearrangement of diastereomerically-defined α-(allyloxy)stannanes.