Enantioselective Carbonylative Cyclization of Alkenes with C–H Bonds for Synthesis of γ-Lactams Bearing an α-Quaternary Carbon
The development of effective synthetic methods to construct γ-lactams bearing a chiral α-quaternary carbon from relatively inert C(O)-H bonds with alkenes has been an elusive challenge. Herein, we used a naphthylamine-derived phosphine oxide ligating Ni and Al bimetallic catalyst to realize a carbonylative cyclization of formyl C-H bonds with alkenes, highly regio- and enantioselectively constructing γ-lactams bearing a chiral α-quaternary carbon in up to 99% yield and 98% ee. These γ-lactams proved to be versatile synthetic precursors for many biologically active molecules.
Authors
- Mengchun Ye (ORCID: https://orcid.org/0000-0002-2019-5365)
- Hao-Rui Wang (ORCID: https://orcid.org/0000-0002-9765-6203)
- Yuqing Jiang
- Genping Huang (ORCID: https://orcid.org/0000-0002-2249-1248)
- Xueyuan Yan (ORCID: https://orcid.org/0000-0001-6206-4083)
- Qi‐Lin Zhou (ORCID: https://orcid.org/0000-0002-4700-3765)
- Yanan Sun (ORCID: https://orcid.org/0000-0003-3678-6255)
- Zhenlong Gao
- Weiwei Xu (ORCID: https://orcid.org/0009-0008-2373-9138)
Institutions
- Tianjin University (CN)
- Nankai University (CN)
- Unité Matériaux et Transformations (FR)
Publication Details
- Journal
- Journal of the American Chemical Society
- Published
- 2024-12-19
- DOI
- https://doi.org/10.1021/jacs.4c15875
- Citations
- 14
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 3.50
Funders
- National Natural Science Foundation of China
- National Key Research and Development Program of China
- Fundamental Research Funds for the Central Universities