Nickel-Catalyzed Electronically Reversed Enantioselective Hydrocarbofunctionalizations of Acrylamides

Dedicated to the 10^th anniversary of the Chemistry Department at SUSTech.

Abstract

Asymmetric hydrocarbofunctionalization of alkenes has emerged as an efficient strategy for synthesizing optically active molecules through a carbon–carbon bond-forming process from readily available alkenes and carboelectrophiles. Here, we present a summary of our efforts to control the regio- and enantioselectivity of hydrocarbofunctionalizations of electron-deficient alkenes with a nickel catalyst and a chiral bisoxazolidine ligand. The reaction permits electron-reversed hydrocarbofunctionalizations of acrylamides with excellent enantioselectivity. This operationally simple protocol permits the asymmetric hydroalkylation, hydrobenzylation, or hydropropargylation of acrylamides. This reaction is useful for preparing a wide range of α-branched chiral amides with broad functional-group tolerance.

Key words

hydroalkylations - hydrobenzylations - hydropropargylations - hydrofunctionalizations - asymmetric catalysis - cross-couplings

Publication History

Received: 01 April 2021

Accepted after revision: 08 April 2021

Accepted Manuscript online:
08 April 2021

Article published online:
03 May 2021

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