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Synlett 1996; 1996(10): 1010-1012
DOI: 10.1055/s-1996-5648
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Consecutive Intramolecular Azomethine Ylid Cycloaddition - Pummerer Rearrangement as a Strategy for the Synthesis of Enantiomerically Pure 5-(Hydroxymethyl)prolines

L. M. Harwood* , I. A. Lilley
  • *Department of Chemistry, Reading University, Whiteknights, Reading RG6 6AD, U.K., Fax +44(118)9318449, e-mail l.m.harwood@reading.ac.uk
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Publication Date:
31 December 2000 (online)

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The thiatricycle (2S, 6R, 8S, 12S)-(2), prepared in one pot by reaction of (5S)-5-phenylmorpholinone with (prop-2-enyl)thioethanal, is converted stereoselectively to sulfoxide (5) which undergoes regio- and stereoselective Pummerer rearrangement. Subsequent elaboration furnishes (2S, 4R, 8S)-5-(hydroxymethyl)-4-methylproline (9).

chiral - azomethine - ylid - Pummerer - 5-(hydroxymethyl)proline