Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 142, Issue 12, Pages 5568-5573Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.0c02441
Keywords
-
Categories
Funding
- National Institutes of Health (NIH) [1R01GM132300-01]
- National Science Foundation (NSF) [CHE-9208463, CHE-9629688]
- NIH [RR08389-01]
- NIH-S10 award [NIH-1S10OD020022-1]
- Spanish MINECO-FEDER [CTQ2016-78205-P, CTQ2016-81797-REDC]
Ask authors/readers for more resources
Amidoallyl cations are appealing three-carbon synthons for the preparation of complex amine-containing carbocycles; however, methods to generate and utilize these reactive species are limited and underexplored compared to those for oxallyl cations. Here we disclose a bioinspired strain-driven ring opening of bicyclic methyleneaziridines to 2-amidopentadienyl cation intermediates that readily engage in Nazarov cyclizations. Advantages of this strategy include ease of generation and improved reactivity compared to 3-pentadienyl cations, control over the ultimate position of the alkene, the potential for high dr between vicinal stereocenters, and the ability to further elaborate the products to fully substituted aminocyclopentanes. Experimental and computational studies support a dual role for the Rh2Ln complex as both a nitrene transfer catalyst and a Lewis acid promoter, insight that provides a framework for the future development of asymmetric 2-imino-Nazarov cyclizations.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available