Electrophilic amination of ketone enolates mediated by the DiTOX asymmetric building block: Enantioselective formal synthesis of alpha-aminoacids

Philip C.. Bulman Page, Michael J. McKenzie, Steven M. Allin, Derek R. Buckle

Research output: Contribution to journalArticle

23 Citations (Scopus)

Abstract

Diastereoselective electrophilic amination of enolates derived from 2-acyl-1,3-dithiane 1-oxides is used as the key step for an enantioselective synthesis of two alpha -hydrazido carboxylic acids, well-known precursors of alpha -amino acids. (C) 2000 Elsevier Science Ltd. All rights reserved.
Original languageEnglish
Pages (from-to)9683-9695
Number of pages13
JournalTetrahedron
Volume56
Issue number49
DOIs
Publication statusPublished - 2000

Keywords

  • ARYLGLYCINES
  • ETHERS
  • ALKYLATION
  • SULFOXIDATION
  • ESTERS
  • HYDRAZINO ACIDS
  • chiral auxiliary
  • 3-DITHIANE 1-OXIDES
  • ACID-DERIVATIVES
  • 1
  • asymmetric synthesis
  • aminoacid
  • STEREOSELECTIVE AMINATION
  • enolate
  • AZODICARBOXYLATE

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