A remarkably stereoselective reduction of a γ-hydroxyketone with two equiv. of lithium triethylborohydride has been observed and this effect has been suggested to originate from ‘chelation control’; the reaction has been utilised in a short stereoselective synthesis of ancistrofuran.
R. Baker, P. D. Ravenscroft and C. J. Swain, J. Chem. Soc., Chem. Commun., 1984, 74 DOI: 10.1039/C39840000074
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