Reaction of carbonyl compounds with sodium borohydride in a two-phase system, in the presence of chiral ammonium salts containing a secondary hydroxy-group affords the corresponding carbinols with 0–32% enantiomeric excess. The optical yields are higher when the hydroxy group is β to the ‘onium’ function and the catalyst is conformationally more rigid.
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Journal of the Chemical Society, Perkin Transactions 1
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