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Chiral Alkyl Amine Synthesis via Catalytic Enantioselective Hydroalkylation of Enecarbamates

Deyun Qian, Srikrishna Bera and Xile Hu*

*Institute of Chemical Sciences and Engineering, École Polytechnique Fédérale de Lausanne (EPFL), ISIC-LSCI, BCH 3305, Lausanne 1015, Switzerland, Email: xile.huepfl.ch

D. Qian, S. Bera, X. Hu, J. Am. Chem. Soc., 2021, 143, 1959-1967.

DOI: 10.1021/jacs.0c11630


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Abstract

A nickel-catalyzed hydroalkylation of enecarbamates (N-Cbz-protected enamines) with alkyl halides provides a wide range of chiral alkyl amines with high regio- and enantioselectivity. The mild conditions lead to high functional group tolerance, which is demonstrated in late-stage modifications of many natural products and drug molecules.

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Key Words

alkylation, pinacolborane


ID: J48-Y2021