Asymmetric synthesis of beta(2)-amino acids: 2-substituted-3-aminopropanoic acids from N-acryloyl SuperQuat derivatives

James E. Beddow, Stephen G. Davies, Kenneth B. Ling, Paul M. Roberts, Angela J. Russell, Andrew D. Smith, James E. Thomson, Andrew David Smith

Research output: Contribution to journalArticlepeer-review

49 Citations (Scopus)

Abstract

Conjugate addition of lithium dibenzylamide to (S)-N(3)-acryloyl-4-isopropyl-5,5-dimethyloxazolidin-2-one ( derived from L-valine) and alkylation of the resultant lithium beta-amino enolate provides, after deprotection, a range of (S)-2-alkyl-3-aminopropanoic acids in good yield and high ee. Alternatively, via a complementary pathway, conjugate addition of a range of secondary lithium amides to (S)-N(3)-(2'-alkylacryloyl)-4-isopropyl-5,5-dimethyloxazolidin-2-ones, diastereoselective protonation with 2-pyridone, and subsequent deprotection furnishes a range of (R)-2-alkyl- and (R)-2-aryl-3-aminopropanoic acids in good yield and high ee. Additionally, the boron-mediated aldol reaction of beta-amino N-acyl oxazolidinones is a highly diastereoselective method for the synthesis of a range of beta-amino-beta'-hydroxy N-acyl oxazolidinones.

Original languageEnglish
Pages (from-to)2812-2825
Number of pages14
JournalOrganic & Biomolecular Chemistry
Volume5
Issue number17
DOIs
Publication statusPublished - 2007

Keywords

  • BETA-AMINO ACIDS
  • HIGHLY DIASTEREOSELECTIVE ADDITION
  • DYNAMIC KINETIC RESOLUTION
  • ENANTIOSELECTIVE SYNTHESIS
  • CONJUGATE ADDITION
  • MICHAEL ADDITION
  • CHIRAL AUXILIARY
  • ORGANIC-SYNTHESIS
  • D-GLYCERALDEHYDE
  • LITHIUM AMIDES

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