A facile three-step synthesis of 1,2-amino alcohols using the Ellman homochiral tert-butylsulfinamide

James C. Barrow, Phung L. Ngo, Janetta M. Pellicore, Harold G. Selnick, Philippe G. Nantermet

Research output: Contribution to journalArticlepeer-review

Abstract

Addition of organometallic reagents to tert-butylsulfinimines derived from tert-butyldimethylsiloxyacetaldehyde stereoselectively generates protected 1,2-amino alcohols. Removal of the acid labile protecting groups affords amino alcohols in high yield. The predominant diastereomer is opposite to that predicted by the traditional Ellman model; therefore, a chelation model invoking rapid E/Z isomerization of the imine is proposed to rationalize the observed selectivity.

Original languageEnglish (US)
Pages (from-to)2051-2054
Number of pages4
JournalTetrahedron Letters
Volume42
Issue number11
DOIs
StatePublished - Mar 11 2001
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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