P, S Ligands for the Asymmetric Construction of Quaternary Stereocenters in Palladium‐Catalyzed Decarboxylative [4+2] Cycloadditions. (6th January 2016)

• Record Type: Journal Article
• Authors: Wei, Yi; Lu, Liang‐Qiu; Li, Tian‐Ren; Feng, Bin; Wang, Qiang; Xiao, Wen‐Jing; Alper, Howard
• Is Part Of: Angewandte Chemie. Volume 128:Number 6(2016)
• Page Start: 2240
• Page End: 2244
• Publication Date: 2016-01-06
• Subjects: Asymmetrische Katalyse -- Cycloadditionen -- Heterocyclen -- Ligandenentwicklung -- Palladium; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201509731
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: A new hybrid P, S ligand was exploited by combining a chiral β‐amino sulfide and a simple diphenyl phosphite. The resultant ligand performs extremely well in a palladium‐catalyzed asymmetric decarboxylative [4+2] cycloaddition reaction, thus generating multiple contiguous stereocenters and a chiral quaternary center. By doing so, a straightforward route to highly functionalized tetrahydroquinolines was developed with yields of up to 99 %, as well as 98 % ee and greater than 95:5 d.r. Moreover, mechanistic insights into this transformation and the possible stereocontrol are discussed.