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■ Stereoselectivity of the Biginelli Reaction Catalyzed by Chiral Primary Amine: A Computational Study

Takayoshi Yoshimura, Maneeporn Puripat, Vudhichai Parasuk, and Miho Hatanaka*

*Department of Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, Kanagawa 223-8522, Japan

Abstract

The Biginelli reaction catalyzed by a chiral compound is one of the most effective ways to form bioactive heterocycle compounds. High enantioselectivity was obtained using primary amine with a chiral diamine backbone as a chiral catalyst. To elucidate the origin of the enantioselectivity, we investigated the reaction pathways of this catalytic reaction using the density functional theory. We also focused on the transition states of the rate-determining step leading different stereoisomers. The rate-determining step was the proton transfer process accompanying the cyclization of the substrate, which was mediated by the amide moiety of the catalyst, and the orientation of the amide moiety was the reason for the enantioselectivity.