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Synlett 1993; 1993(8): 599-601
DOI: 10.1055/s-1993-22545
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Evaluation of Non-Racemic Glycidol Derivatives in the Asymmetric Synthesis of Cyclopropanemethanols

David J. Aitken* , Fabrice Vergne, Ai Savanh Phimmanao, Dominique Guillaume, Henri-Philippe Husson
  • *Laboratoire de Chimie Thérapeutique, URA 1310 du CNRS, Faculté des Sciences Pharmaceutiques et Biologiques, 4 Avenue de l'Observatoire, F-75270 Paris Cedex 06, France
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Publication Date:
19 March 2002 (online)

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A series of non-racemic glycidol derivatives bearing C-1 leaving groups was assessed for reactivity in the cyclopropane-methanol forming reaction with N,N-dibenzylaminoacetonitrile under basic conditions. Glycidyl benzenesulfonate, epichlorohydrin, epibromohydrin and glycidyl triflate gave increasingly good yields and C-1 regioselectivity, while other sulfonate esters were completely unreactive.