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Stephenson manuscript.pdf (389.57 kB)
Bridged Bicyclic Building Block Upgrading: Photochemical Synthesis of bicyclo[3.1.1]heptan-1-Amines
Preprints are manuscripts made publicly available before they have been submitted for formal peer review and publication. They might contain new research findings or data. Preprints can be a draft or final version of an author's research but must not have been accepted for publication at the time of submission.
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.