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

Zhe Lu, Ashraf Wilsily and Gregory C. Fu*

*Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States, Email: gcfmit.edu

Z. Lu, A. Wilsily, G. C. Fu, J. Am. Chem. Soc., 2011, 133, 8154-8157.

DOI: 10.1021/ja203560q

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Abstract

In stereoconvergent, arylamine-directed alkyl-alkyl Suzuki cross-coupling reactions, structure-enantioselectivity studies are consistent with the nitrogen, not the aromatic ring, serving as the primary site of coordination of the arylamine to the catalyst.

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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

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

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Key Words

Suzuki Coupling, Alkyl-Alkyl Coupling, Amines

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ID: J48-Y2011-1580