Stereodivergent Approach to α-Hydroxy Acids Involving Substrate Directed Reduction of α-Keto Amides

Article abstract of DOI:10.1016/00404-0399(50)11528-

Substrate directed reduction of 'S'-2-hydroxymethylpyrrolidine derived α-keto amides with tetramethylammonium triacetoxyborohydride proceeds with good stereoselectivity at room temperature.A reversal of stereoselectivity is observed in reductions with conventional borohydride reducing agents in protic solvents.