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Synlett 1991; 1991(4): 273-275
DOI: 10.1055/s-1991-20706
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Unusual Stereofacial Differentiation in the Reduction of Bicyclo[3.1.0]hexanones by Luche's Reagent (NaBH4-CeCl3)

A. Krief* , D. Surleraux
  • *Department of Chemistry, Facultés Notre Dame de la Paix, 61 rue de Bruxelles, B-5000 Namur, Belgium
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Publication Date:
07 March 2002 (online)

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Cerium(III) chloride as well as some other lanthanide salts invert the stereoselectivity of the reduction of bicylco[3.1.0]hexane-2,4-diones and bicyclo[3.1.0]hexan-2-ones 1 by sodium borohydride in methanol so as to favour attack of the hydride from the most hindered, concave face of these molecules to give exo-4-hydroxybicyclo[3.1.0]hexan-2-ones and exo-bicyclo-[3.1.0]hexan-1-ols, respectively, in excellent yield.