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Chiral Metal Nanoparticle Systems as Heterogeneous Catalysts beyond Homogeneous Metal Complex Catalysts for Asymmetric Addition of Arylboronic Acids to α,β-Unsaturated Carbonyl Compounds

Tomohiro Yasukawa, Aya Suzuki, Hiroyuki Miyamura, Kohei Nishino and Shu̅ Kobayashi*

*Department of Chemistry, School of Science, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan, Email: shu_kobayshichem.s.u-tokyo.ac.jp

T. Yasukawa, A. Suzuki, H. Miyamura, K. Nishino, S. Kobayashi, J. Am. Chem. Soc., 2015, 137, 6616-6623.

DOI: 10.1021/jacs.5b02213 (free Supporting Information)


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Abstract

Asymmetric Rh-catalyzed 1,4-addition of arylboronic acids to α,β-unsaturated carbonyl compounds proceeded smoothly to afford the corresponding β-arylated products in excellent yields and outstanding enantioselectivities with wide substrate scope. Remarkably, a chiral metal nanoparticle system showed performance in terms of yield, enantioselectivity, and catalytic turnover that was superior. This catalyst can be recovered and reused.

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Key Words

1,4-addition


ID: J48-Y2015