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Chemical science
Nov 01, 2015;6 (11): 6224-6229.

Cellulose-supported chiral rhodium nanoparticles as sustainable heterogeneous catalysts for asymmetric carbon-carbon bond-forming reactions.

Tomohiro Yasukawa, Hiroyuki Miyamura, Shū Kobayashi
Author Information
  1. Tomohiro Yasukawa: Department of Chemistry , School of Science , The University of Tokyo , Hongo, Bunkyo-ku , Tokyo 113-0033 , Japan . Email: shu_kobayashi@chem.s.u-tokyo.ac.jp.
  2. Hiroyuki Miyamura: Department of Chemistry , School of Science , The University of Tokyo , Hongo, Bunkyo-ku , Tokyo 113-0033 , Japan . Email: shu_kobayashi@chem.s.u-tokyo.ac.jp.
  3. Shū Kobayashi: Department of Chemistry , School of Science , The University of Tokyo , Hongo, Bunkyo-ku , Tokyo 113-0033 , Japan . Email: shu_kobayashi@chem.s.u-tokyo.ac.jp.
PMID: 30090239 DOI: 10.1039/c5sc02510a

Abstract

Cellulose-supported chiral Rh nanoparticle (NP) catalysts have been developed. The Rh NPs, which were well dispersed on cellulose, catalyzed the asymmetric 1,4-addition of arylboronic acids to enones and enoates, one of the representative asymmetric carbon-carbon bond-forming reactions, in the presence of chiral diene ligands, providing the corresponding adducts in high yields with outstanding enantioselectivities without metal leaching. The solid-state NMR analysis of the chiral NP system directly suggested interactions between the Rh NPs and the chiral ligand on cellulose. This is the first example of using polysaccharide-supported chiral metal nanoparticles for asymmetric carbon-carbon bond-forming reactions.

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Journal Article

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