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Chiral Alkyl Amine Synthesis via Catalytic Enantioselective Hydroalkylation of Enamides

preprint
submitted on 15.10.2020 and posted on 16.10.2020 by Deyun Qian, Srikrishna Bera, Xile Hu
Chiral alkyl amines are omnipresent as bio-active molecules and synthetic intermediates. Catalytic and enantioselective synthesis of alkyl amines from readily accessible precursors is challenging. Here we develop a nickel-catalyzed hydroalkylation method to assemble a wide range of chiral alkyl amines from enamides and alkyl halides in high regio- and enantioselectivity. The method works for both non-activated and activated alkyl halides, and is able to produce enantiomerically enriched amines with two minimally differentiated alpha-alkyl substituents. The mild conditions lead to high functional group tolerance, which is demonstrated in the post-product functionalization of many natural products and drug molecules, as well as the synthesis of chiral building blocks and key intermediates to bio-active compounds.

History

Email Address of Submitting Author

xile.hu@epfl.ch

Institution

EPFL

Country

Swittzerland

ORCID For Submitting Author

0000-0001-8335-1196

Declaration of Conflict of Interest

none

Exports