Chiral oxime ethers in asymmetric synthesis. 3. Asymmetric synthesis of (R)-N-protected alpha-amino acids by the addition of organometallic reagents to the ROPHy oxime of cinnamaldehyde

C J Moody, P T Gallagher, A P Lightfoot, A M Z Slawin

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49 Citations (Scopus)

Abstract

A new asymmetric synthesis of a-amino acids is described in which the key step is the diastereoselective addition of organometallic reagents to (R)-O-(1-phenylbutyl)cinnamaldoxime 5 to give hydroxylamines 6. Subsequent reductive cleavage of the N-O bond in the hydroxylamine 6 followed by N-protection gave the carbamates 7, which upon oxidation with ruthenium(III) chloride/periodate gave the N-protected amino acids 8. The method was also adapted to the synthesis of a quaternary amino acid 15 from the ketoxime ether 9.

Original languageEnglish
Pages (from-to)4419-4425
Number of pages7
JournalThe Journal of Organic Chemistry
Volume64
Issue number12
Publication statusPublished - 11 Jun 1999

Keywords

  • DIASTEREOSELECTIVE ALKYLATION
  • CYCLIC DIPEPTIDE
  • RELAY AUXILIARY
  • ALDOXIMES
  • ORGANOLITHIUMS
  • REARRANGEMENT
  • DERIVATIVES
  • ALLYLATION
  • CATALYSIS
  • BROMIDE

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