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C2-Symmetric Chiral Disulfoxide Ligands in Rhodium-Catalyzed 1,4-Addition: From Ligand Synthesis to the Enantioselection Pathway


Mariz, Ronaldo; Poater, Albert; Gatti, Michele; Drinkel, Emma; Bürgi, Justus J; Luan, Xinjun; Blumentritt, Sascha; Linden, Anthony; Cavallo, Luigi; Dorta, Reto (2010). C2-Symmetric Chiral Disulfoxide Ligands in Rhodium-Catalyzed 1,4-Addition: From Ligand Synthesis to the Enantioselection Pathway. Chemistry - A European Journal, 16(48):14335-14347.

Abstract

A family of chiral C2-symmetric disulfoxide ligands possessing biaryl atropisomeric backbones has been synthesized by using the Andersen methodology. Complete characterization includes X-ray crystallographic studies of all ligands and some of their rhodium complexes. Their synthesis, optical purity, electronic properties, and catalytic behavior in the prototypical rhodium-catalyzed 1,4-addition of phenylboronic acid to 2-cyclohexen-1-one are presented through an in depth study of this ligand class. Density functional theory calculations on the step of the catalytic cycle that determines the enantioselectivity are presented and reinforce the first hypothetical explanations for the high levels of asymmetric induction observed.

Abstract

A family of chiral C2-symmetric disulfoxide ligands possessing biaryl atropisomeric backbones has been synthesized by using the Andersen methodology. Complete characterization includes X-ray crystallographic studies of all ligands and some of their rhodium complexes. Their synthesis, optical purity, electronic properties, and catalytic behavior in the prototypical rhodium-catalyzed 1,4-addition of phenylboronic acid to 2-cyclohexen-1-one are presented through an in depth study of this ligand class. Density functional theory calculations on the step of the catalytic cycle that determines the enantioselectivity are presented and reinforce the first hypothetical explanations for the high levels of asymmetric induction observed.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2010
Deposited On:11 Dec 2012 17:08
Last Modified:05 Apr 2016 16:10
Publisher:Wiley-VCH Verlag Berlin
Series Name:Chemistry - A European Journal
ISSN:0947-6539
Funders: Alfred Werner Assistant Professorship, Swiss National Science Foundation, Roche Research Foundation, Ramón y Cajal contract by the Spanish MEC
Publisher DOI:https://doi.org/10.1002/chem.201001749

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