Synthesis of Axially Chiral QUINAP Derivatives by Ketone‐Catalyzed Enantioselective Oxidation

Author:

Jiang Peng‐Ying12,Wu San2,Wang Guan‐Jun2,Xiang Shao‐Hua2,Tan Bin2ORCID

Affiliation:

1. Harbin Institute of Technology Harbin 150001 China

2. Shenzhen Grubbs Institute Department of Chemistry Southern University of Science and Technology Shenzhen 518055 China

Abstract

AbstractQUINAPs have emerged as a pivotal class of axially chiral compounds with remarkable features in the stereoinduction of diverse enantioselective transformations. However, the confined substrate range and extravagant price still pose challenges, limiting their broader utilization. Herein, we describe the first atroposelective oxidation of an N atom using a chiral ketone catalyst, allowing the kinetic resolution of QUINAPOs to give both the unreacted substrates and their corresponding N‐oxides with excellent enantioselectivity. Importantly, the enantioenriched products can be readily converted into the QUINAP targets without any loss of stereochemical integrity. Mechanistic investigations indicate that a dioxirane, generated through the oxidation of the ketone with oxone, acts as the active catalytic species. Furthermore, we have successfully extended this catalytic system to the kinetic resolution of QUINOLs and the dynamic kinetic transformation of pyridine analogues of QUINAPO possessing a labile stereogenic axis. The practicality of the developed protocol is further demonstrated by the successful application of QUINAPO N‐oxide as a Lewis base catalyst in a series of enantioselective transformations.

Funder

National Natural Science Foundation of China

Publisher

Wiley

Subject

General Medicine

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