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Synlett 1991; 1991(10): 747-749
DOI: 10.1055/s-1991-34770
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N,N-Dibenzylaminoacetonitrile, a Highly Efficient Synthon for the Synthesis of (±)-cis- and (±)-trans-2,3-Methanohomoserines

Dominique Guillaume* , David J. Aitken, H. -P. Husson
  • *Laboratoire de Chimie Thérapeutique, URA 1310 du CNRS, Faculté de Sciences Pharmaceutiques et Biologiques, 4 Avenue de l'Observatoire, F-75270 Paris Cedex 06, France
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Publication Date:
13 March 2002 (online)

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α-Aminonitriles are effectively alkylated with epibromohydrin (bromomethyloxirane) in contrast to their glycine ester analogues which do not react at all; thus (dibenzylamino)acetonitrile (3a) serves as an excellent synthon for the preparation of (±)-cis- and (±)-trans-2,3-methanohomoserines (10;1-amino-2-hydroxymethylcyclopropanecarboxylic acids). The key step involves tandem alkylation/intramolecular cyclization of 3a with epibromohydrin in the presence of strong base (lithium diisopropylamide/hexamethylphosphoric triamide) to yield 1-dibenzylamino-2-hydroxymethylcyclopropanecarbonitrile (3d) as a 1:1 mixture of cis/trans isomers