The [2,3]-Wittig rearrangements of lithioalkyl allyl ethers exhibited different cis,trans selectivities than [2,3] shifts in their lithiomethyl analogues

Article abstract of DOI:10.1016/S0040-4020(01)89348-0

The reductive lithiation of O,S-acetals 9a-d initiated [2,3]-Wittig rearrangements whose cis-trans-selectivity depended on whether lithiomethyl (→ cis) or lithioalkyl allyl ethers reacted (→ trans). It is suggested that these rearrangements proceed via mi