Stereoselective Reduction of Carbonyl Compounds by use of Carbohydrate Auxiliaries

S. Krishna Mohan*

Department of Chemistry, School of Science The University of Tokyo, Hongo 7-3-1, Bunkyo-ku, Tokyo 113-0033 (Japan)

Propargyl derivatives such as 2, 5, 12, 13, 19, 22, 27 and 31 were converted to corresponding keto auxiliaries on reaction with mercuric triflouroacetate in 2:1 acetone water system. These compounds were subjected to asymmetric reduction by using metal hydrides like 1) sodium borohydride, MeOH, 0°C, 2) sodium borohydride, CeCl3, 7H2O, MeOH, 0°C, 3) lithium aluminium hydride, THF, 0°C and 4) zinc borohydride, Et2O, 0°C.

Propargyl derivatives; Keto auxiliaries