Abstract
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.