Asymmetric Reduction of Heteroaryl Methyl Ketones Using Daucus carota英文文献资料.docVIP

Green and Sustainable Chemistry, 2011, 1, 117-122 doi:10.4236/gsc.2011.14019 Published Online November 2011 (http://www.SciRP.org/journal/gsc) Asymmetric Reduction of Heteroaryl Methyl Ketones Using Daucus carota Ch Sree Lakshmi, Goka Roopa Reddy, Adari Bhaskar Rao * Organic Chemistry Division, Indian Institute of Chemical Technology, Hyderabad, India E-mail: adarirao2002@yahoo.co.in Received July 7, 2011; revised August 26, 2011; accepted September 13, 2011 * Abstract Asymmetric reduction of the heteroaryl prochiral ketones to corresponding chiral alcohols by Daucus carota was studied. The study highlights selective bioreduction of different substituted heteroaryl ketones ( 1a - 1j) to their respective chiral alcohols ( 2a - 2j) using plant dehydrogenase enzymes present in Daucus carota in good yields (60% - 95%) and enantioselectivity (76% - 99%) with S-form configuration. The results obtained confirm that the membrane bound dehydrogenase enzyme has broad substrate specificity and selectivity in catalyzing both six and five membered heteroaryl methyl ketones. The present methodology demonstrates promising and alternative green route in the synthesis secondary chiral alcohols of biologically importance in a simple, inexpensive and eco-friendly process. Keywords: Daucus carota, Bio-Reduction, Chiral Alcohols, Enantioselectivity 1. Introduction aromatic components of foods, perfumes and smoking suppressants. Chiral heteroaryl alcohols have numerous applications as important intermediates in the synthesis of biological active molecules and also act as chiral li- gands/auxiliaries in a number of asymmetric addition re- actions [7-9]. There are many reports describing syn- thesis of chiral secondary alcohols using biocatalysts ob- tained from microbial/different parts of plant tissues [10-12].The asymmetric reductions of heteroaryl methyl ketones is a straight forward approach and a large num- ber of chemical