Inversion of Configuration in the Displacement of Lithium by Hydrogen during a Transannular 1,4-Hydrogen Transfer Accompanying a -Wittig Rearrangement

Article abstract of DOI:10.1021/jo00030a008

The presence of a 4-tert-butyl group on 2-lithio-6-(trans-1-propenyl)tetrahydropyran dramatically changes the rearrangement behavior, inhibiting the formation of <2,3>-Wittig rearrangement product and leading to a 1,4-transannular H-transfer to the lithium-bearing carbon atom with inversion of configuration.