Unusual Stereofacial Differentiation in the Reduction of Bicyclo[3.1.0]hexanones by Luche's Reagent (NaBH4-CeCl3)
- 1 January 1991
- journal article
- letter
- Published by Georg Thieme Verlag KG in Synlett
- Vol. 1991 (04) , 273-275
- https://doi.org/10.1055/s-1991-20706
Abstract
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.Keywords
This publication has 0 references indexed in Scilit: