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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: gcfmit.edu

A. Wilsily, F. Tramutola, N. A. Owston, G. C. Fu, J. Am. Chem. Soc., 2012, 134, 5794-5797.

DOI: 10.1021/ja301612y (free Supporting Information)


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.

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Stereoconvergent Amine-Directed Alkyl-Alkyl Suzuki Reactions of Unactivated Secondary Alkyl Chlorides

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