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Synlett 2001; 2001(10): 1599-1601
DOI: 10.1055/s-2001-17449
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Asymmetric Synthesis of α-Amino Carbonyls (Aldehydes, Ketones and Acids) using Lithium (R)-N-benzyl-N-α-methylbenzylamide

Stephen G. Davies* , Simon W. Epstein, Osamu Ichihara, Andrew D. Smith
  • *The Dyson Perrins Laboratory, University of Oxford, South Parks Road, Oxford, OX1 3QY, UK; Fax + 44(0)18 65 27 56 33; E-mail: steve.davies@chemistry.ox.ac.uk
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Publication Date:
27 September 2001 (online)

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The diastereoselective conjugate addition of lithium (R)-N-benzyl-N-α-methylbenzylamide to α,β-unsaturated esters and subsequent enolate hydroxylation, followed by reduction and oxidative cleavage provides a facile route to N,N-protected α-amino aldehydes and ketones. Further manipulation furnishes α-amino acids in high enantiomeric excess.

β-amino acids - conjugate addition - lithium amides - asymmetric synthesis - α-amino aldehyde - α-amino acid

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