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Synlett 2001; 2001(12): 1836-1840
DOI: 10.1055/s-2001-18762
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An Acetone-derived Chiral Stabilised Azomethine Ylid: Synthesis of Enantiomerically Pure 5,5,-Dimethylproline Derivatives

David J. Aldous* , Michael G. B. Drew, Estelle M.-N. Hamelin, Laurence M. Harwood, Archie B. Jahans, Sukanthini Thurairatnam
  • *Rhône Poulenc Rorer Limited, Rainham Road South, Dagenham, Essex RM10 7XS, UK; Fax: + 44 (118) 9316782; E-mail: l.m.harwood@reading.ac.uk
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Publication History

Publication Date:
04 December 2001 (online)

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The chiral stabilised azomethine ylid 3 generated in situ via Lewis acid catalysed condensation of (5S)-5-phenylmorpholin-2-one with 2,2-dimethoxypropane can be trapped diastereoselectively with singly and doubly activated dipolarophiles. The cycloadducts may be dismantled in one pot to furnish enantiomerically pure 5,5-dimethylproline derivatives.

ketone-derived chiral stabilised azomethine ylid - 5,5-dimethylprolines - Lewis acid

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