Synthesis of chromans and kinetic resolution of 2-aryl-3-nitro-2H-chromenes via the NHC-bound azolium homoenolate pathway. Issue 20 (28th August 2019)

• Record Type: Journal Article
• Authors: Bhattacharya, Aditya; mani Shukla, Pushpendra; Kumar Kaushik, Lalit; Maji, Biswajit
• Is Part Of: Organic chemistry frontiers. Volume 6:Issue 20(2019)
• Page Start: 3523
• Page End: 3529
• Publication Date: 2019-08-28
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/c9qo00868c
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : Herein, an effective kinetic resolution (KR) of racemate 2-aryl-3-nitro-2 H -chromenes to afford synthetically valuable chromans and 2 H -chromenes through an NHC-bound acyl azolium homoenolate pathway has been demonstrated. Abstract : Beyond the tandem oxa-Michael strategy, an N-heterocyclic carbene-catalyzed kinetic resolution approach to access highly diastereo- and enantioenriched 2-aryl-3-nitro-chromane derivatives has been developed. An efficient strategy for the kinetic resolution of racemic 2-aryl-3-nitro-2 H -chromenes was also successfully achieved. This catalytic kinetic resolution method allows the synthetically valuable chiral scaffolds, chromane and 2 H -chromene, to be accessed in a single catalytic and asymmetric transformation, through the NHC-bound azolium homoenolate pathway.