A Chiral Disulfoxide Ligand for the Efficient Rhodium-Catalyzed 1,2-Addition of Arylboroxines to N-Tosylarylimines

Guangzhen Zhao, Gellert Sipos, A. Salvador, Arnold Ou, Pengchao Gao, Brian Skelton, Reto Dorta

Research output: Contribution to journalArticle

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53 Downloads (Pure)

Abstract

© 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.Enantiomerically pure diarylmethylamines are important building blocks in active pharmaceutical ingredients. Herein, we report a rhodium precatalyst with a chiral disulfoxide ligand that effects the 1,2-addition of arylboroxines to aromatic imines to give high yields and high enantioselectivities of these products. The present paper describes a system that is very simple, where the ease of synthesis of the chiral ligand is combined with low catalyst loadings and reaction conditions that do not need any additives or external base.
Original languageEnglish
Pages (from-to)1759-1766
JournalAdvanced Synthesis and Catalysis
Volume358
Issue number11
Early online date26 Jan 2016
DOIs
Publication statusPublished - 2 Jun 2016

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Rhodium
Ligands
Imines
Enantioselectivity
Catalysts
Pharmaceutical Preparations

Cite this

Zhao, Guangzhen ; Sipos, Gellert ; Salvador, A. ; Ou, Arnold ; Gao, Pengchao ; Skelton, Brian ; Dorta, Reto. / A Chiral Disulfoxide Ligand for the Efficient Rhodium-Catalyzed 1,2-Addition of Arylboroxines to N-Tosylarylimines. In: Advanced Synthesis and Catalysis. 2016 ; Vol. 358, No. 11. pp. 1759-1766.
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A Chiral Disulfoxide Ligand for the Efficient Rhodium-Catalyzed 1,2-Addition of Arylboroxines to N-Tosylarylimines. / Zhao, Guangzhen; Sipos, Gellert; Salvador, A.; Ou, Arnold; Gao, Pengchao; Skelton, Brian; Dorta, Reto.

In: Advanced Synthesis and Catalysis, Vol. 358, No. 11, 02.06.2016, p. 1759-1766.

Research output: Contribution to journalArticle

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AU - Zhao, Guangzhen

AU - Sipos, Gellert

AU - Salvador, A.

AU - Ou, Arnold

AU - Gao, Pengchao

AU - Skelton, Brian

AU - Dorta, Reto

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AB - © 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.Enantiomerically pure diarylmethylamines are important building blocks in active pharmaceutical ingredients. Herein, we report a rhodium precatalyst with a chiral disulfoxide ligand that effects the 1,2-addition of arylboroxines to aromatic imines to give high yields and high enantioselectivities of these products. The present paper describes a system that is very simple, where the ease of synthesis of the chiral ligand is combined with low catalyst loadings and reaction conditions that do not need any additives or external base.

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