Dynamic kinetic resolution of β′-keto-β-amino esters using Ru–DTBM–Sunphos catalyzed asymmetric hydrogenation

Xiaoming Li; Xiaoming Tao; Xin Ma; Wanfang Li; Mengmeng Zhao; Xiaomin Xie; Tahar Ayad; Virginie Ratovelomanana-Vidal; Zhaoguo Zhang

doi:10.1016/j.tet.2013.05.136

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Dynamic kinetic resolution of β′-keto-β-amino esters using Ru–DTBM–Sunphos catalyzed asymmetric hydrogenation

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Dynamic kinetic resolution of β′-keto-β-amino esters using Ru–DTBM–Sunphos catalyzed asymmetric hydrogenation

Xiaoming Li, Xiaoming Tao, Xin Ma, Wanfang Li, Mengmeng Zhao, Xiaomin Xie, Tahar Ayad, Virginie Ratovelomanana-Vidal et Zhaoguo Zhang

Tetrahedron, Vol.69(34), pp.7152-7156

26/08/2013

DOI: https://doi.org/10.1016/j.tet.2013.05.136

Résumé

Asymmetric hydrogenation

Carbapenem

Dynamic kinetic resolution

A convenient method for the enantioselective synthesis of β′-hydroxy-β-amino esters was developed through intensive investigations of the reaction conditions. Dichloromethane (DCM)/2,2,2-trifluoroethanol (TFE) and 1,2-dichloroethane (DCE)/TFE combinations were found to be the appropriate co-solvents for the reaction. In this mixed solvent system, [Ru(cymene)Cl2]2–Sunphos exhibited unusually higher activity and selectivity than the corresponding [Ru(cymene)I2]2–Sunphos. In situ generated catalyst could be used for this transformation. Asymmetric hydrogenation of a series of β′-keto-β-amino esters derivatives using Ru–Sunphos complexes via dynamic kinetic resolution led to the corresponding β′-hydroxy-β-amino esters with ee up to 99.6% and de up to 98.8% (S/C=1000). [Display omitted]

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Titre: Dynamic kinetic resolution of β′-keto-β-amino esters using Ru–DTBM–Sunphos catalyzed asymmetric hydrogenation
Créateurs - sans rôle: Xiaoming Li - School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, China
Xiaoming Tao - School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, China
Xin Ma - School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, China
Wanfang Li - School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, China
Mengmeng Zhao - School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, China
Xiaomin Xie - School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, China
Tahar Ayad - Chimie ParisTech
Virginie Ratovelomanana-Vidal - Chimie ParisTech
Zhaoguo Zhang - School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, China
Détails de publication: Tetrahedron, Vol.69(34), pp.7152-7156
Éditeur: Elsevier Ltd
Nombre de pages: 5
Identifiants: 99158392709311
Unité académique: Institut Charles Gerhardt Montpellier - ICGM
Langue: English
Type de ressource: Journal article