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Asymmetric conjugate addition of organometallic reagents in the presence of tertiary amines to chiral alpha beta unsaturated amidocarboxylic acids addition order of reagents as an unprecedented factor in the determination of the sense of asymmetric induction



Asymmetric conjugate addition of organometallic reagents in the presence of tertiary amines to chiral alpha beta unsaturated amidocarboxylic acids addition order of reagents as an unprecedented factor in the determination of the sense of asymmetric induction



Journal of the Chemical Society Perkin Transactions I (5): 759-764



Optically active 3-substituted carboxylic acids have been obtained in moderate enantiomeric excesses (e.e.) by asymmetric conjugate addition of alkyl-lithium, in the presence of tertiary amines, to chiral .alpha.,.beta.-unsaturated amido carboxylic acids derived from (S)-proline. The presence of tertiary amine is effective in increasing both the synthetic yields and the e.e's. A change in the addition order of tertiary amine and alkyl-lithium to the amido-carboxylic acid changes the sense of asymmetric induction.

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Accession: 004792107

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