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  • [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.

[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.

Chemistry (Weinheim an der Bergstrasse, Germany) (2009-03-21)
Michiko Sasaki, Hidaka Ikemoto, Masatoshi Kawahata, Kentaro Yamaguchi, Kei Takeda
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
n-Butyllithium solution, 2.7 M in heptane
Sigma-Aldrich
n-Butyllithium solution, 2.5 M in hexanes
Sigma-Aldrich
n-Butyllithium solution, 11.0 M in hexanes
Sigma-Aldrich
n-Butyllithium solution, 2.0 M in cyclohexane
Sigma-Aldrich
n-Butyllithium solution, 1.6 M in hexanes
Sigma-Aldrich
n-Butyllithium solution, 1.4 M in toluene