Premium
Heterogeneous Chiral Diene‐Rh Complexes for Asymmetric Arylation of α,β‐Unsaturated Carbonyl Compounds, Nitroalkenes, and Imines
Author(s) -
Kuremoto Tatsuya,
Yasukawa Tomohiro,
Kobayashi Shū
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201900526
Subject(s) - chemistry , diene , moiety , amide , alkyl , ligand (biochemistry) , amine gas treating , yield (engineering) , catalysis , medicinal chemistry , organic chemistry , biochemistry , natural rubber , receptor , materials science , metallurgy
A chiral diene ligand with tertiary alkyl amine‐derived secondary amide moiety was immobilized on cross‐linked polystyrene (PS) by radical polymerization, which was combined with Rh to form heterogeneous chiral Rh complexes (PS‐diene Rh−Cl). PS‐diene Rh−Cl catalyzed asymmetric arylation reactions of α,β‐unsaturated carbonyl compounds (ketones, esters, and amides), nitroalkenes, and imines afforded the desired products in high yields with excellent enantioselectivities. PS‐diene Rh−Cl is stable in air, can be stored for several months, and can be reused more than 10 times without any reduction of either yield or enantioselectivity. We also developed a method of activation of PS‐diene Rh−Cl to generate more active species.