Issue 45, 2017

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

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

Supplementary files

Article information

Article type
Communication
Submitted
22 Mar 2017
Accepted
12 May 2017
First published
12 May 2017

Chem. Commun., 2017,53, 6113-6116

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, 53, 6113 DOI: 10.1039/C7CC02156A

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