CONSECUTIVE INTRAMOLECULAR AZOMETHINE YLID CYCLOADDITION - PUMMERER REARRANGEMENT AS A STRATEGY FOR THE SYNTHESIS OF ENANTIOMERICALLY PURE 5-(HYDROXYMETHYL)PROLINES

Authors
HARWOOD LM LILLEY IA
Citation
Lm. Harwood et Ia. Lilley, CONSECUTIVE INTRAMOLECULAR AZOMETHINE YLID CYCLOADDITION - PUMMERER REARRANGEMENT AS A STRATEGY FOR THE SYNTHESIS OF ENANTIOMERICALLY PURE 5-(HYDROXYMETHYL)PROLINES, Synlett, (10), 1996, pp. 1010
Citations number
9
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synlett → ACNP
ISSN journal
09365214
Issue
10
Year of publication
1996
Database
ISI
SICI code
0936-5214(1996):10<1010:CIAYC->2.0.ZU;2-1
Abstract
The thiatricycle (2S, 6R, 8S, 12S)-(2), prepared in one pot by reactio n of (5S)-5-phenylmorpholinone with (prop-2-enyl)thioethanal, is conve rted stereoselectively to sulfoxide (5) which undergoes regio- and ste reoselective Pummerer rearrangement. Subsequent elaboration furnishes (2S, 4R, 5S)-5-(hydroxymethyl)-4-methylproline (9).