Synthesis of enantiomerically pure tertiary 1,2-aminoalcohols by the highly diastereoselective reductive ring opening of oxazolidines

Philip C. Bulman Page, Benjamin R. Buckley, Mark R. J. Elsegood, Colin M. Hayman, Harry Heaney, Gerasimos A. Rassias, Salem A. Talib, John Liddle

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Abstract

A number of enantiomerically pure 1,2-aminoalcohols containing tertiary nitrogen atoms bearing chiral substituents have been prepared by highly diastereoselective reductive ring cleavage of oxazolidines derived from ketones and pseudoephedrine or ephedrine. The ring cleavage occurs with retention of configuration. (c) 2007 Elsevier Ltd. All rights reserved.
Original languageEnglish
Pages (from-to)10991-10999
Number of pages9
JournalTetrahedron
Volume63
Issue number45
DOIs
Publication statusPublished - 2007

Keywords

  • enantiomerically pure
  • aminoalcohol
  • KETONES
  • reductive cleavage
  • CLEAVAGE
  • AMINATION
  • oxazolidine
  • CONJUGATE ADDITION
  • HYDRIDE
  • stereoselective
  • PSEUDOEPHEDRINE
  • DERIVATIVES
  • OXAZOLINES
  • reduction
  • EPHEDRINE

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