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Integrated Process of Aerobic Oxidation–Olefination–Asymmetric CC Bond Formation Catalyzed by Robust Heterogeneous Gold/Palladium and Chirally Modified Rhodium Nanoparticles
Author(s) -
Miyamura Hiroyuki,
Suzuki Aya,
Yasukawa Tomohiro,
Kobayashi Shū
Publication year - 2015
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.201500529
Subject(s) - chemistry , rhodium , palladium , bimetallic strip , catalysis , tandem , nanoparticle , aqueous solution , combinatorial chemistry , colloidal gold , organic chemistry , nanotechnology , materials science , composite material
We have achieved an integrated process of oxidation–olefination–asymmetric 1,4‐addition reactions under aerobic and aqueous conditions using metal nanoparticles as robust heterogeneous catalysts. A tandem process of aerobic oxidation and Horner–Wadsworth–Emmons olefination was successfully catalyzed by gold/palladium bimetallic nanoparticles. A wide range of substrates gave the desired products in high yields and excellent selectivities. This tandem process was further connected with an asymmetric 1,4‐addition reaction catalyzed by chiral rhodium nanoparticles to achieve a challenging three‐step, one‐pot sequential reaction. Various types of esters with a chiral center at the β‐position were obtained from readily available and stable alcohols and arylboronic acids in high yields with high enantioselectivities in a one‐pot sequential reaction integrating three transformations.