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We have shown that connection of C-2 of an allylsilane to a tethered aziridine ring yields exocyclic γ-amino olefins and desilylated azabicyclo[x.2.1]-systems upon cyclization with BF 3 .OEt 2 . Furthermore, manipulation of a specific exocyclic γ-amino olefin provided access to an azabicyclo[3.3.1]nonane. This methodology should be useful for the preparation of natural products and...
Bicyclic proline analogs have a wide range of biological uses. We report here our synthesis of bicyclic proline analogs using a formal [3+2] intramolecular aziridine-allylsilane cycloaddition reaction. This synthesis allows for the preparation of both 5-5 and 6-5 fused ring systems and should be amenable to the preparation of analogs with substitution on the carbocyclic ring.
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