Asymmetric electrophilic syntheses using chiral acyclic imidate ester enolates. Highly enantioselective syntheses of carboxylic acid esters
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Chiral imidate esters (RCH2C(OEt)=NR⋆; R = Me, Et; R⋆ = (S)-CH(CH2Ph)CH2OCH3, (R)-CH(Ph)-CH2OCH3, (S)-CH(i-Pr)CH2OCH3) were prepared and deprotonated with various bases to give the corresponding lithio anion derivatives. Alkylations of the lithio derivatives proceeded in high synthetic yield and with good to excellent asymmetric induction to give, α,α-disubstituted carboxylic acid derivatives. The structures of the imidate esters and their lithio derivatives are discussed. © 1984, American Chemical Society. All rights reserved.
author list (cited authors)
Gluchowski, C., Tiner-Harding, T., Smith, J. K., Bergbreiter, D. E., & Newcomb, M.