Asymmetric Hydrogenation of α-Ketoesters on Chirally Modified Pt Catalysts Supported on MPC-61 Ordered Mesoporous Carbon

Chem. J. Chinese Universities ›› 2011, Vol. 32 ›› Issue (6): 1354.

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Asymmetric Hydrogenation of α-Ketoesters on Chirally Modified Pt Catalysts Supported on MPC-61 Ordered Mesoporous Carbon

LI Kai-Xiang, LI Xiao-Hong*, SONG Li-Ying, WU Peng

Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, Shanghai 200062, China

Received:2010-11-04 Revised:2011-03-28 Online:2011-06-10 Published:2011-05-10
Contact: LI Xiao-Hong E-mail:xhli@chem.ecnu.edu.cn
Supported by:
国家自然科学基金(批准号: 20703018)、国家“九七三”计划项目(批准号: 2006CB202508)和上海市科委科技启明星人才计划项目(批准号: 08QA1402700)资助.

Abstract

Abstract: 4% and 10% (mass fraction) Pt catalysts supported on MPC-61, a kind of ordered mesoporous carbon, were prepared by an impregnation method using two different Pt precursors, ethanolic solution and aqueous solution of H2PtCl6. These Pt/MPC-61 catalysts were characterized by XRD, N2-sorption, TEM and CO chemisorption. The Pt/MPC-61catalysts proved to be efficient in the asymmetric hydrogenation of ethyl pyruvate after chirally modified with cinchonidine. The Cat-4Pt-E catalyst derived from the ethanolic solution of H2PtCl6 afforded better conversions of ethyl pyruvate due to smaller Pt particle size with higher Pt dispersion. While the Cat-4Pt-W catalysts derived from the aqueous solution of H2PtCl6 showed higher chiral induction ability. The catalyst Cat-4Pt-W-150 that was calcined at 150 oC under vacuum gave higher conversion and higher enantioselectivity than Cat-4Pt-W did, the highest TOF reaching 8820 h-1 in water. A 66% ee value was furnished by Cat-10Pt-E catalyst in acetic acid. In particular, the Cat-4Pt-W catalyst showed superior catalytic activity to the commercial Pt/C catalyst, mainly due to the ordered mesoporous structure features of MPC-61 support. The 4% Pt catalysts supported on MPC-61 can also be effectively applied in the asymmetric hydrogenation of ethyl 2-oxo-4-phenylbutyrate, of which the hydrogenation product can be used to produce A.C.E inhibitors. Under the optimal conditions, the catalyst Cat-4Pt-W-150 gave a 61% ee value of (R)-(+)-ethyl 2-hydroxyl-4-phenylbutyrate.

Key words: Ordered mesoporous carbon, Pt catalyst, Cinchonidine, a-Ketoesters, Asymmetric hydrogenation

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LI Kai-Xiang, LI Xiao-Hong*, SONG Li-Ying, WU Peng. Asymmetric Hydrogenation of α-Ketoesters on Chirally Modified Pt Catalysts Supported on MPC-61 Ordered Mesoporous Carbon[J]. Chem. J. Chinese Universities, 2011, 32(6): 1354.

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Asymmetric Hydrogenation of α-Ketoesters on Chirally Modified Pt Catalysts Supported on MPC-61 Ordered Mesoporous Carbon

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