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Bridged Bicyclic Building Block Upgrading: Photochemical Synthesis of bicyclo[3.1.1]heptan-1-Amines

preprint
submitted on 20.10.2020, 16:17 and posted on 21.10.2020, 09:10 by Alexander Harmata, Madison Sowden, Corey Stephenson
Compounds containing bridged bicyclic carbon skeletons are desirable building blocks for medicinal chemistry. However, as a result of their inefficient, linear syntheses, commercially available compounds of this sort are plagued by high costs and/or a lack of diversity in substitution patterns. Herein we report the conversion of the readily available bicyclo[1.1.1]pentan-1-amine substructure to a wide range of poly-substituted bicyclo[3.1.1]pentan-1-amines using imine photochemistry. To our knowledge, this is the first reported method to convert the bicyclo[1.1.1]pentane skeleton to the bicyclo[3.1.1]heptane skeleton. Hydrolysis of the imine products gives complex, sp3-rich primary amine building blocks.

Funding

Photochemical synthesis of bioactive molecules

National Institute of General Medical Sciences

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History

Email Address of Submitting Author

crjsteph@umich.edu

Institution

University of Michigan

Country

USA

ORCID For Submitting Author

0000-0002-2443-5514

Declaration of Conflict of Interest

None

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