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P,S Ligands for the Asymmetric Construction of Quaternary Stereocenters in Palladium‐Catalyzed Decarboxylative [4+2] Cycloadditions
Author(s) -
Wei Yi,
Lu LiangQiu,
Li TianRen,
Feng Bin,
Wang Qiang,
Xiao WenJing,
Alper Howard
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201509731
Subject(s) - stereocenter , ligand (biochemistry) , palladium , sulfide , catalysis , chemistry , combinatorial chemistry , cycloaddition , stereochemistry , enantioselective synthesis , organic chemistry , biochemistry , receptor
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.
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