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A dynamic kinetic asymmetric transfer hydrogenation–cyclization tandem reaction: an easy access to chiral 3,4-dihydro-2H-pyran-carbonitriles

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Abstract

A chiral (mesitylene)RuCl(monosulfonated diamine) catalysed dynamic kinetic resolution (DKR)–asymmetric transfer hydrogenation (ATH) process is developed for highly enantio- (up to 99% ee) and diastereo- (up to 98 : 2 dr) selective reduction of challenging racemic α-aryl-γ-keto malononitriles. A spontaneous cyclization reaction of the hydrogenation products delivers a cascade process for efficient synthesis of useful enantioenriched 3,4-dihydro-2H-pyran-carbonitriles.

Graphical abstract: A dynamic kinetic asymmetric transfer hydrogenation–cyclization tandem reaction: an easy access to chiral 3,4-dihydro-2H-pyran-carbonitriles

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Publication details

The article was received on 22 Mar 2017, accepted on 12 May 2017 and first published on 12 May 2017


Article type: Communication
DOI: 10.1039/C7CC02156A
Citation: Chem. Commun., 2017, Advance Article
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    A dynamic kinetic asymmetric transfer hydrogenation–cyclization tandem reaction: an easy access to chiral 3,4-dihydro-2H-pyran-carbonitriles

    D. Zheng, Q. Zhao, X. Hu, T. Cheng, G. Liu and W. Wang, Chem. Commun., 2017, Advance Article , DOI: 10.1039/C7CC02156A

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