Chiral Nanoparticles/Lewis Acids as Cooperative Catalysts for Asymmetric 1,4-Addition of Arylboronic Acids to α,β-Unsaturated Amides

Tomohiro Yasukawa; Yuuki Saito; Hiroyuki Miyamura; Shū Kobayashi

doi:10.1002/anie.201601559

Chiral Nanoparticles/Lewis Acids as Cooperative Catalysts for Asymmetric 1,4-Addition of Arylboronic Acids to α,β-Unsaturated Amides

Angew Chem Int Ed Engl. 2016 Jul 4;55(28):8058-61. doi: 10.1002/anie.201601559. Epub 2016 May 19.

Authors

Tomohiro Yasukawa¹, Yuuki Saito¹, Hiroyuki Miyamura¹, Shū Kobayashi²

Affiliations

¹ Department of Chemistry, School of Science, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo, 113-0033, Japan.
² Department of Chemistry, School of Science, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo, 113-0033, Japan. shu_kobayashi@chem.s.u-tokyo.ac.jp.

PMID: 27193210
DOI: 10.1002/anie.201601559

Abstract

Cooperative catalysts consisting of chiral Rh/Ag nanoparticles and Sc(OTf)3 have been developed that catalyze asymmetric 1,4-addition reactions of arylboronic acids with α,β-unsaturated amides efficiently. The reaction has been considered one of the most challenging reactions because of the low reactivity of the amide substrates. The new catalysts provide the desired products with outstanding enantioselectivities (>98 % ee) in the presence of low loadings (<0.5 mol %) of the catalyst.

Keywords: Lewis acid; Rh catalysis; cooperative effects; heterogeneous catalysis; nanoparticles.

Publication types

Research Support, Non-U.S. Gov't