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A chiral bis-sulfoxide ligand in late-transition metal catalysis; rhodium-catalyzed asymmetric addition of arylboronic acids to electron-deficient olefins


Mariz, R; Luan, X; Gatti, M; Linden, A; Dorta, R (2008). A chiral bis-sulfoxide ligand in late-transition metal catalysis; rhodium-catalyzed asymmetric addition of arylboronic acids to electron-deficient olefins. Journal of the American Chemical Society, 130(7):2172-2173.

Abstract

A bis-sulfoxide with a binaphthyl backbone is introduced as a readily available, chiral ligand entity in late-transition metal catalysis. Ligand p-tol-BINASO [where p-tol-BINASO is 1,1‘-binaphthalene-2,2‘-diyl-bis-(p-tolylsulfoxide)] is obtained in pure form in one single synthetic step from relatively cheap, commercially available starting materials. Precatalyst [{(P,R,R)-p-tol-BINASO}RhCl]2 was synthesized in high yield and structurally characterized by X-ray diffraction, and structural data were compared to the free ligand. The precatalyst shows both excellent reactivity and selectivity in the asymmetric 1,4-addition of arylboronic acids to cyclic α,β-unsaturated ketones and esters.

Abstract

A bis-sulfoxide with a binaphthyl backbone is introduced as a readily available, chiral ligand entity in late-transition metal catalysis. Ligand p-tol-BINASO [where p-tol-BINASO is 1,1‘-binaphthalene-2,2‘-diyl-bis-(p-tolylsulfoxide)] is obtained in pure form in one single synthetic step from relatively cheap, commercially available starting materials. Precatalyst [{(P,R,R)-p-tol-BINASO}RhCl]2 was synthesized in high yield and structurally characterized by X-ray diffraction, and structural data were compared to the free ligand. The precatalyst shows both excellent reactivity and selectivity in the asymmetric 1,4-addition of arylboronic acids to cyclic α,β-unsaturated ketones and esters.

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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:February 2008
Deposited On:15 Feb 2009 10:57
Last Modified:05 Apr 2016 12:58
Publisher:American Chemical Society
ISSN:0002-7863
Publisher DOI:https://doi.org/10.1021/ja710665q
PubMed ID:18220399

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