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 o...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2024-12, p.e202413695
Main Authors: Harmata, Alexander S, Tatunashvili, Elene, Chang, Abigail, Wang, Tao, Stephenson, Corey R J
Format: Article
Language:English
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Summary: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.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.202413695