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Synlett 1996; 1996(11): 1051-1053
DOI: 10.1055/s-1996-5682
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Synthesis of Homochiral α-Substituted Alanine Derivatives by Diastereocontrolled Alkylation of (5R)-5-Phenyl-3-methyl-3,4-dehydromorpholinones

L. M. Harwood* , K. J. Vines, M. G. B. Drew
  • *Department of Chemistry, University of Reading, Whiteknights, READING RG6 6AD, U.K., Telephone +44 (0)1189 318449, Fax +44 (0)1189 316782, Email l.m.harwood@reading.ac.uk
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Publication Date:
31 December 2000 (online)

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Dehydromorpholinones, 1a-d, have been prepared by direct condensation of (R9-phenylglycinol with α-ketoesters in refluxing trifluoroethanol. Chemo- and diastereoselective alkylation of the imine moiety 1a furnished trisubstituted morpholinones, 4, and subsequent cleavage of the cyclic template revealed homochiral α-substituted alanine derivatives, 5.

morpholinone - diastereoselective alkylation - α-substituted alanine

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