Palladium-Catalyzed Enantioselective C-H Olefination of Diaryl Sulfoxides through Parallel Kinetic Resolution and Desymmetrization

Yu-Chao Zhu; Yan Li; Bo-Chao Zhang; Feng-Xu Zhang; Yi-Nuo Yang; Xi-Sheng Wang

doi:10.1002/anie.201801146

Palladium-Catalyzed Enantioselective C-H Olefination of Diaryl Sulfoxides through Parallel Kinetic Resolution and Desymmetrization

Angew Chem Int Ed Engl. 2018 Apr 23;57(18):5129-5133. doi: 10.1002/anie.201801146. Epub 2018 Mar 23.

Authors

Yu-Chao Zhu¹, Yan Li¹, Bo-Chao Zhang¹, Feng-Xu Zhang¹, Yi-Nuo Yang¹, Xi-Sheng Wang¹

Affiliation

¹ Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, Center for Excellence in Molecular Synthesis of CAS, University of Science and Technology of China, Hefei, Anhui, 230026, China.

PMID: 29512253
DOI: 10.1002/anie.201801146

Abstract

The first example of Pd^II -catalyzed enantioselective C-H olefination with non-chiral or racemic sulfoxides as directing groups was developed. A variety of chiral diaryl sulfoxides were synthesized with high enantioselectivity (up to 99 %) through both desymmetrization and parallel kinetic resolution (PKR). This is the first report of Pd^II -catalyzed enantioselective C(sp² )-H functionalization through PKR, and it represents a novel strategy to construct sulfur chiral centers.

Keywords: C−H activation; desymmetrization; palladium; parallel kinetic resolution; sulfoxide.

Publication types

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