Homochiral Lithium Amides for the Asymmetric Synthesis of b-Amino Acids

S G Davies, N M Garrido, D Kruchinin, O Ichihara, L J Kotchie, P D Price, A J Price-Mortimer, A J Russell, Andrew David Smith

Research output: Contribution to journalArticlepeer-review

78 Citations (Scopus)

Abstract

Secondary homochiral lithium amides derived from a-methylbenzylamine undergo highly diastereoselective conjugate additions to a range of alpha,beta-unsaturated esters. The corresponding beta-amino acids are readily liberated by successive N-debenzylation and ester hydrolysis, furnishing (R)-beta-amino butyric acid, (R)-beta-amino pentanoic acid, (S)-beta-leucine, (R)-beta-amino octanoic acid, (S)-beta-phenylalanine, (S)-beta-tyrosine methyl ether, (S)-beta-tyrosine hydrochloride and (S)-beta-(2-methoxyphenyl)-beta-amino propanoic acid in high yields and high ee. The application of this procedure to the synthesis of the natural products (R)-beta-DOPA and (R)-beta-lysine is demonstrated. The development of a simplified one-pot reaction protocol applicable to the multi-gram scale synthesis of homochiral beta-amino esters is also delineated. (c) 2006 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)1793
Number of pages1793
JournalTetrahedron: Asymmetry
Volume17
DOIs
Publication statusPublished - 31 Jul 2006

Keywords

  • ENANTIOSELECTIVE SYNTHESIS
  • CONJUGATE ADDITION
  • ORGANIC-SYNTHESIS
  • ALPHA,BETA-UNSATURATED ESTERS
  • MICHAEL ADDITIONS
  • STEREOSELECTIVE-SYNTHESIS
  • NITROGEN NUCLEOPHILES
  • PRACTICAL SYNTHESIS
  • IRON COMPLEXES
  • MARINE SPONGE

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