[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.
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.
Sasaki
Michiko
M
Graduate School of Medical Sciences, Hiroshima University, 1-2-3 Kasumi, Minami-Ku, Hiroshima, Japan.
Ikemoto
Hidaka
H
Kawahata
Masatoshi
M
Yamaguchi
Kentaro
K
Takeda
Kei
K
D000838:Anions / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry; D013237:Stereoisomerism
D000838:Anions; D009942:Organometallic Compounds; C046771:butyllithium; D002244:Carbon