Palladium‐Catalyzed Enantioselective C−H Olefination of Diaryl Sulfoxides through Parallel Kinetic Resolution and Desymmetrization. Issue 18 (23rd March 2018)

• Record Type: Journal Article
• Authors: Zhu, Yu‐Chao; Li, Yan; Zhang, Bo‐Chao; Zhang, Feng‐Xu; Yang, Yi‐Nuo; Wang, Xi‐Sheng
• Is Part Of: Angewandte Chemie international edition. Volume 57:Issue 18(2018)
• Page Start: 5129
• Page End: 5133
• Publication Date: 2018-03-23
• Subjects: desymmetrization -- C−H activation -- palladium -- parallel kinetic resolution -- sulfoxide; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201801146
• Languages: English
• ISSNs: 1433-7851

Abstract

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(sp 2 )−H functionalization through PKR, and it represents a novel strategy to construct sulfur chiral centers. Abstract : A 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 through both desymmetrization and parallel kinetic resolution (PKR). This is the first reported Pd II ‐catalyzed enantioselective C(sp 2 )−H functionalization through PKR, and it represents a novel strategy to construct sulfur chiral centers.