An Enantioselective Approach to 4-O-Protected-2-cyclopentene-l,4-diol Derivatives via a Rhodium-Catalyzed Redox-Isomerization Reaction

Kai Ren; Mengmeng Zhao; Bei Hu; Bin Lu; Xiaomin Xie; Virginie Ratovelomanana-Vidal; Zhaoguo Zhang

doi:10.1021/acs.joc.5b02519

An Enantioselective Approach to 4-O-Protected-2-cyclopentene-l,4-diol Derivatives via a Rhodium-Catalyzed Redox-Isomerization Reaction

J Org Chem. 2015 Dec 18;80(24):12572-9. doi: 10.1021/acs.joc.5b02519. Epub 2015 Dec 9.

Authors

Kai Ren¹, Mengmeng Zhao¹, Bei Hu¹, Bin Lu¹, Xiaomin Xie¹, Virginie Ratovelomanana-Vidal², Zhaoguo Zhang^{1

3}

Affiliations

¹ School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University , 800 Dongchuan Road, Shanghai 200240, P. R. China.
² PSL Research University , Chimie ParisTech-CNRS, Institut de Recherche de Chimie Paris, 75005 Paris, France.
³ State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry , 345 Lingling Road, Shanghai 200032, P. R. China.

PMID: 26605977
DOI: 10.1021/acs.joc.5b02519

Abstract

Kinetic resolution of a series of cyclopentene-1,4-diol derivatives has been successfully achieved with enantiomeric excess up to 99.4% and a kf/ks ratio of 55 by a rhodium-catalyzed redox-isomerization reaction in a noncoordinating solvent.

Publication types

Research Support, Non-U.S. Gov't