Abstract
Chiral-auxiliary-mediated synthesis represents the most frequently used synthetic
tool for the induction of chirality on α-position of γ-lactams in organic synthesis.
However, the general strategy requires the stoichiometric use of chiral reagents with
multiple manipulation steps. Transition-metal-catalyzed asymmetric alkene dicarbofunctionalization
using readily available substrates under mild conditions allows the simultaneous construction
of two vicinal chemical bonds and a chiral carbon center, hence, gain expedient access
to chiral heterocycles. Herein, we disclose a Ni-catalyzed enantioselective reaction
of 3-butenyl carbamoyl chloride and primary alkyl iodide enabled by a newly designed
chiral 8-quinoline imidazoline ligand (8-Quinim). This protocol features broad functional
group tolerance and high enantioselectivities, achieving unprecedented synthesis of
chiral nonaromatic heterocycles via catalytic reductive protocol.
1 Introduction
2 Development of 8-Quinim Ligand
3 Nickel/8-Quinim-Catalyzed Enantioselective Synthesis of Chiral α-Alkylated γ-Lactam
4 Conclusion and Outlook
Key words
8-Quinim - nickel catalysis - reductive coupling - unactivated alkene - dicarbofunctionalization
- chiral α-alkylated γ-lactam synthesis
