New Directing Groups for Metal-Catalyzed Asymmetric Carbon-Carbon Bond-Forming Processes: Stereoconvergent Alkyl-Alkyl Suzuki Cross-Couplings of Unactivated Electrophiles
Ashraf Wilsily, Francesco Tramutola, Nathan A. Owston and Gregory C. Fu*
*Department of Chemistry, Massachusetts Institute of
Technology, Cambridge, Massachusetts 02139, United States, Email: gcf
mit.edu
A. Wilsily, F. Tramutola, N. A. Owston, G. C. Fu, J. Am. Chem. Soc., 2012, 134, 5794-5797.
DOI: 10.1021/ja301612y
Abstract
Carbamates and sulfonamides serve as directing groups in Ni-catalyzed asymmetric Suzuki reactions for cross-coupling of unactivated alkyl electrophiles. Racemic secondary bromides and chlorides undergo C-C bond formation in a stereoconvergent process in good ee at room temperature in the presence of a commercially available Ni complex and chiral ligand.
see article for more examples
Z. Lu, A. Wilsily, G. C. Fu, J. Am. Chem. Soc., 2011, 133, 8154-8157.
Key Words
Suzuki Coupling, Alkyl-Alkyl Coupling, Amines
ID: J48-Y2012-0990
