ChemRxiv
These are preliminary reports that have not been peer-reviewed. They should not be regarded as conclusive, guide clinical practice/health-related behavior, or be reported in news media as established information. For more information, please see our FAQs.
1/1
3 files

Catalytic, Enantioselective α-Alkylation of Azlactones with Non-Conjugated Alkenes via Directed Nucleopalladation

preprint
submitted on 08.11.2018 and posted on 08.11.2018 by Sri Nimmagadda, Mingyu Liu, Malkanthi Karunananda, De-Wei Gao, Omar Apolinar, Jason Chen, Peng Liu, Keary Engle
A palladium(II)-catalyzed enantioselective α-alkylation of azlactones with non-conjugated alkenes is described. The reaction employs a chiral BINOL-derived phosphoric acid as the source of stereoinduction and a cleavable bidentate directing group appended to the alkene to control regioselectivity and stabilize the nucleopalladated alkylpalladium(II) intermediate in the catalytic cycle. A wide range of azlactones were found to be compatible under the optimal conditions to afford products bearing α,α-disubstituted α-amino acid derivatives with high yields and high enantioselectivity.

Funding

NIH-5R35GM125052-02, NIH-1R35GM128779, NSF-DBI-1759544

History

Email Address of Submitting Author

keary@scripps.edu

Institution

The Scripps Research Institute

Country

USA

ORCID For Submitting Author

0000-0003-2767-6556

Declaration of Conflict of Interest

No conflict of interest to declare.

Exports