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An Insoluble Copper(II) Acetylacetonate-Chiral Bipyridine Complex that Catalyzes Asymmetric Silyl Conjugate Addition in Water

Taku Kitanosono, Lei Zhu, Chang Liu, Pengyu Xu and Shu̅ Kobayashi*

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

T. Kitanosono, L. Zhu, C. Liu, P. Xu, S. Kobayashi, J. Am. Chem. Soc., 2015, 137, 15422-15425.

DOI: 10.1021/jacs.5b11418


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Abstract

A water-insoluble copper(II) acetylacetonate-chiral bipyridine complex catalyzed an asymmetric silyl conjugate addition of lipophilic substrates in water. Indeed, the reactions proceeded efficiently only in water. Water seems to play a role in constructing and stabilizing sterically confined transition states and accelerating subsequent protonation.

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Key Words

silylation


ID: J48-Y2015