Bicyclo[2.1.1]hexanes via Intramolecular Formal (3+2)‐Cycloaddition
Abstract 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)
- Abigail Chang
- Tao Wang (ORCID: https://orcid.org/0009-0003-1825-0163)
Institutions
- Merck & Co., Inc., Rahway, NJ, USA (United States) (US)
- University of British Columbia (CA)
- University of Michigan (US)
Publication Details
- Journal
- Angewandte Chemie
- Published
- 2024-10-11
- DOI
- https://doi.org/10.1002/ange.202413695
- Primary Topic
- Oxidative Organic Chemistry Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.00