title: [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 alpha-oxy-benzylcarbanion through a double bond.
abstract: Don't get trapped: The effect of conjugating electron-withdrawing groups and alpha-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).The effect of conjugating electron-withdrawing groups and alpha-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.
authors.affiliation: Graduate School of Medical Sciences, Hiroshima University, 1-2-3 Kasumi, Minami-Ku, Hiroshima, Japan.
authors.forename: Michiko
authors.initials: M
authors.lastname: Sasaki
authors.forename: Hidaka
authors.initials: H
authors.lastname: Ikemoto
authors.forename: Masatoshi
authors.initials: M
authors.lastname: Kawahata
authors.forename: Kentaro
authors.initials: K
authors.lastname: Yamaguchi
authors.forename: Kei
authors.initials: K
authors.lastname: Takeda
mesh_terms: D000838:Anions / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000838:Anions; D009942:Organometallic Compounds; C046771:butyllithium; D002244:Carbon