Bicyclo[2.1.1]hexanes via Intramolecular Formal (3+2)‐Cycloaddition
We report a synthesis of bicyclo[2.1.1]hexanes via an intramolecular formal (3+2) cycloaddition of allylated cyclopropanes bearing a 4-nitrobenzimine substituent. Both activated and unactivated alkenes are tolerated in the transformation. The bicyclic imine products are prone to photo-induced ring opening, allowing for the epimerization of C5-stereogenic compounds.
Authors
- Corey R. J. Stephenson (ORCID: https://orcid.org/0000-0002-2443-5514)
- Elene Tatunashvili
- Alexander S. Harmata (ORCID: https://orcid.org/0000-0003-3646-407X)
- Tao Wang (ORCID: https://orcid.org/0000-0002-5866-8148)
- Abigail Chang
Institutions
- Merck & Co., Inc., Rahway, NJ, USA (United States) (US)
- University of British Columbia (CA)
- University of Michigan (US)
Publication Details
- Journal
- Angewandte Chemie International Edition
- Published
- 2024-10-11
- DOI
- https://doi.org/10.1002/anie.202413695
- Citations
- 8
- Primary Topic
- Cyclopropane Reaction Mechanisms
- Type
- article
- Field-Weighted Citation Impact
- 2.00
Funders
- National Science Foundation
- National Institutes of Health
- National Institute of General Medical Sciences