Abstract
This thesis dealt with the catalytic asymmetric borane reduction of prochiral ketones using in situ generated oxazaborolidine derived from (1S,2R,4R)-1-amino-7,7-dimethyl-bicyclo[2.2.1]heptan-2-ol. In the asymmetric reduction, we found the factors which affected the enantioselectivity including the structure and the loading amount of catalyst, the reduction temperature, the substrate, etc. The best experimental conditions found for the asymmetric reduction requires the use of 10 mol% of catalyst, prepared by stirring 0.1eq 1,2-amino alcohol 14 with 1.1eq BH3•SMe2 in THF at 60oC for 0.5hr, followed by dropwise addition of the substrate at the same temperature. Optically active secondary alcohols were obtained in good chemical yields and up to 92% ee.