Formation of All-Carbon Quaternary Centers via Enantioselective Pd-Catalyzed α-Vinylation of γ-Lactams
Herein, we report an enantioselective vinylation of α-substituted γ-lactams that forges quaternary centers in up to 59% yield with 94% ee. The use of canonically inactive vinyl chloride electrophiles afforded the highest yields and levels of stereoselectivity, and a range of trisubstituted vinyl chlorides were found to be proficient in promoting this transformation. These stereogenic products could be further elaborated to functionally rich scaffolds, thereby highlighting the synthetic utility of this process.
Authors
- Farbod A. Moghadam (ORCID: https://orcid.org/0009-0005-4442-2349)
- Melinda Chan (ORCID: https://orcid.org/0000-0002-2495-0110)
- Brian M. Stoltz (ORCID: https://orcid.org/0000-0001-9837-1528)
- Shunya Sakurai (ORCID: https://orcid.org/0000-0003-1331-2794)
- Jay P. Barbor (ORCID: https://orcid.org/0000-0003-2787-4923)
- Carina Jette
Institutions
- California Institute of Technology (US)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-09-03
- DOI
- https://doi.org/10.1021/acs.orglett.4c02551
- Citations
- 10
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 2.50
Funders
- California Institute of Technology
- Heritage Medical Research Institute
- National Institute of General Medical Sciences