ENANTIOSELECTIVE REDUCTION OF A-BROMO AROMATIC KETONES USING CARROT CELLS

摘要

Chiral 1-aryl-2-bromo alcohols with special functional groups on the aromatic ring arepotentially valuable synthetic intermediates for the synthesis of drugs, agrochemicals, flavors andpigments. These chiral alcohols can be obtained from the enantioselective reduction of prochiralaromatic ketones by biological methods. Among these biological methods, microbes and plant cellcultures are more useful than isolated enzymes due to the existence of many enzymes that catalyzevarious reactions. In addition, the use of microbes and plant cell cultures is particularlyadvantageous for carrying out the desired reduction since they do not require the addition ofcofactors for their regeneration. By comparison, less attention has been given to the use of plantcell cultures as a potential enzyme source for catalyzing selected organic reactions. In this paper,the enantioselective reduction of α-bromo aromatic ketones was carried out by using carrot cellcultures and the corresponding chiral 1-aryl-2-bromo alcohols with special functional groups wereproduced. After the reaction conditions were optimized, these chiral 1-aryl-2-bromo alcohols wereobtained with good yields and excellent enantiomeric excesses under the optimal conditions.Meanwhile, the steric factors and electronic effects of the substituents on the aromatic ring wereshown to have an interesting influence on both yield and enantioselectivity in our experiment.