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

Dongsong Zheng; Qiankun Zhao; Xiaoying Hu; Tanyu Cheng; Guohua Liu; Wei Wang

doi:10.1039/c7cc02156a

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

Chem Commun (Camb). 2017 Jun 1;53(45):6113-6116. doi: 10.1039/c7cc02156a.

Authors

Dongsong Zheng¹, Qiankun Zhao, Xiaoying Hu, Tanyu Cheng, Guohua Liu, Wei Wang

Affiliation

¹ Laboratory of Resource Chemistry of Ministry of Education, Shanghai Normal University, Shanghai 200234, China. ghliu@shnu.edu.cn.

PMID: 28530302
DOI: 10.1039/c7cc02156a

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.