P,S Ligands for the Asymmetric Construction of Quaternary Stereocenters in Palladium-Catalyzed Decarboxylative [4+2] Cycloadditions

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 q...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2016-02, Vol.55 (6), p.2200-2204
Main Authors: Wei, Yi, Lu, Liang-Qiu, Li, Tian-Ren, Feng, Bin, Wang, Qiang, Xiao, Wen-Jing, Alper, Howard
Format: Article
Language:English
Subjects:
asymmetric catalysis
cycloaddition
heterocycles
ligand design
palladium
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Summary: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. Hybrid ligands: By combining a chiral β‐amino sulfide and a simple diphenyl phosphite, a new hybrid P,S ligand was used for title reaction. By doing so, multiple contiguous stereocenters and a chiral quaternary center were rapidly constructed and highly functionalized tetrahydroquinolines were produced in up to 99 % yield with 98 % ee and greater than 95:5 d.r.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201509731