Enantioselective addition of diethyl zinc to aldehydes with Chiral Ionic Liquids

ORGN 159

Sanjay V. Malhotra, malhotra@njit.edu1, Yun Wang2, and Yamini H. Patel2. (1) Department of Chemistry and Environmental Science, New Jersey Institute of Technology, University Heights, Newark, NJ 07102, (2) Chemistry and Environmental Science, New Jersey Institute of Technology, University Heights, Newark, NJ 07102
Novel Chiral Ionic Liquids (ChirILs) have been synthesized from natural product, alpha-pinene. These materials are found to be effective in achieving enatioselective C-C bond formation, in the absence of any additional chiral auxiliary. A test study on the addition of diethylzinc to various aldehydes in the presence of ChirILs gives products with moderate to high enantioselctivity and yields. Since both isomers of alpha-pinene are readily available, it is advantages to use such chiral auxiliary to obtain essential isomer of the chiral ionic liquid, and thereby, desired chiral product. This study demonstrates a new approach to chiral synthesis with chiral ionic liquids.