Abstract
Reduction of eight aryl ketones with borane complexes containing (−)(S)-2,2′dihydroxy-1,1′-binapthyl as a chiral auxiliary yielded (with one exception) (R)-alcohols with enantiomeric purities up to 54% (as determined with chiral NMR-shift reagents and/or by enantioselective chromatography on triacetyl-cellulose). In two cases addition of aromatic amines caused a significant increase of e.e. together with a reversal of the absolute chirality (fromR toS). Models for a possible transition state are discussed.
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