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Synlett 2001; 2001(12): 1841-1842
DOI: 10.1055/s-2001-18763
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N-(1′-Benzotriazolylmethyl)-5-phenylmorpholin-2-one: A Stable Crystalline Chiral Azomethine Ylid Precursor

David J. Aldous* , Estelle M.-N. Hamelin, Laurence M. Harwood, 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 Date:
04 December 2001 (online)

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The crystalline adduct of (5S)-5-phenylmorpholin-2-one with formaldehyde and benzotriazole on treatment with acid generates an azomethine ylid which may be trapped with a range of dipolarophiles in yields superior to those using in situ generation methodology.

chiral - azomethine ylid - benzotriazole - dipolar cycloaddition

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