[2,3]‐Wittig Rearrangement of Enantiomerically Enriched 3‐Substituted 1‐Propenyloxy‐1‐phenyl‐2‐propen‐1‐yl Carbanions: Effect of Heteroatoms and Conjugating Groups on Planarization of an α‐Oxy‐Benzylcarbanion through a Double Bond
1. Graduate School of Medical Sciences, Hiroshima University, 1‐2‐3 Kasumi, Minami‐Ku, Hiroshima 734‐8553 (Japan), Fax: (+81)?82‐257‐5184;2. Tokushima Bunri University, 1314‐1 Shido, Sanuki, Kagawa, 769‐2193 (Japan)
Abstract:
Don't get trapped : The effect of conjugating electron‐withdrawing groups and α‐anion‐stabilizing heteroatom substituents on configurational stability of chiral carbanions through a double bond was examined on the basis of extent of chirality transfer in intramolecular trapping in [2,3]‐Wittig rearrangement of chiral 3‐substituted 1‐propenyloxy‐1‐phenyl‐2‐propen‐1‐yl carbanions (see scheme).
