Chromium(III)-Catalyzed Desymmetrization of meso-Epoxides via Remote Stereocontrol: Synthesis of Chiral Fluorenes Bearing All-Carbon Quaternary Stereocenters

Ying Zhou; Feng Jiang; Xin Yue; Xi Wang; Wengang Guo

doi:10.1021/acs.orglett.3c04144

Chromium(III)-Catalyzed Desymmetrization of meso-Epoxides via Remote Stereocontrol: Synthesis of Chiral Fluorenes Bearing All-Carbon Quaternary Stereocenters

Org Lett. 2024 Feb 2;26(4):877-882. doi: 10.1021/acs.orglett.3c04144. Epub 2024 Jan 24.

Authors

Ying Zhou¹, Feng Jiang¹, Xin Yue¹, Xi Wang², Wengang Guo¹

Affiliations

¹ School of Petrochemical Engineering, Changzhou University, Changzhou, Jiangsu 213164, P. R. China.
² School of Materials Engineering, Changzhou Institute of Light Industry Technology, Changzhou, Jiangsu 213164, P. R. China.

PMID: 38264979
DOI: 10.1021/acs.orglett.3c04144

Abstract

An asymmetric desymmetrization of fluorene-derived meso-epoxides is disclosed for the construction of chiral fluorenes bearing an all-carbon quaternary stereocenter at C9. This desymmetrization is catalyzed by a chiral (salen)Cr^III complex via remote stereocontrol, producing diverse chiral fluorenes with excellent yields and stereoselectivity. The practicality of this protocol was demonstrated through the transformation of the obtained products to some intriguing enantioenriched polymerizable monomers.