Enantioselective protonation/diastereoselective reduction with sodium naphthalenide-acetamide; a new synthesis of chiral trans-2-phenylcyclohexanol

Article abstract of DOI:10.1016/S0040-4039(99)00615-2

An efficient synthesis of trans-2-phenylcyclohexanol has been achieved by enantioselective protonation of the enolate of 2-phenylcyclohexanone with α-sulfinyl alcohols and subsequent reduction of the chiral ketone by sodium naphthalenide in the presence of acetamide. Interestingly, the chirality source is not consumed in the synthesis of the chiral target.