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Catalyst‐Controlled Regiodivergent and Enantioselective Formal Hydroamination of N,N‐Disubstituted Acrylamides to α‐Tertiary‐α‐Aminolactam and β‐Aminoamide Derivatives

Herein, a catalyst-controlled regiodivergent and enantioselective formal hydroamination of N,N-disubstituted acrylamides has been developed. Sterically-disfavored and electronically-disfavored enantioselective hydroaminations of electron-deficient alkenes were obtained using different transition metals (Cu, Ni) and chiral ligands, delivering enantioenriched α-tertiary-α-aminolactam and β-aminoamide derivatives in good yields and selectivity.


Abstract

Enantioenriched α-tertiary-α-aminoacid and α-chiral-β-aminoacid derivatives play an important role in biological science and pharmaceutical chemistry. Thus, the development of methods for their synthesis is highly valuable and yet remains challenging. Herein, an unprecedented catalyst-controlled regiodivergent and enantioselective formal hydroamination of N,N-disubstituted acrylamides with aminating agents has been developed, accessing enantioenriched α-tertiary-α-aminolactam and α-chiral-β-aminoamide derivatives. Sterically-disfavored and electronically-disfavored enantioselective hydroamination of electron-deficient alkenes have been successfully tuned using different transition metals and chiral ligands. Notably, extremely hindered aliphatic α-tertiary-α-aminolactam derivatives were synthesized by Cu−H catalyzed asymmetric C−N bond forming with tertiary alkyl species. Enantioenriched α-chiral-β-aminoamide derivatives have been accessed by Ni−H catalyzed anti-Markovnikov-selective formal hydroaminations of alkenes. This set of reactions tolerates a wide range of functional groups to deliver diverse α-tertiary-α-aminolactam and α-chiral-β-aminoamide derivatives in good yields with high levels of enantioselectivity.

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