Sulfone-substituted
bicyclo[1.1.0]butanes and housanes have found
widespread application in organic synthesis due to their bench stability
and high reactivity in strain-releasing processes in the presence
of nucleophiles or radical species. Despite their increasing utility,
their preparation typically requires multiple steps in low overall
yield. In this work, we report an expedient and general one-pot procedure
for the synthesis of 1-sulfonylbicyclo[1.1.0]butanes from readily
available methyl sulfones and inexpensive epichlorohydrin via the
dialkylmagnesium-mediated formation of 3-sulfonylcyclobutanol intermediates.
Furthermore, the process was extended to the formation of 1-sulfonylbicyclo[2.1.0]pentane
(housane) analogues when 4-chloro-1,2-epoxybutane was used as the
electrophile instead of epichlorohydrin. Both procedures could be
applied on a gram scale with similar efficiency and are shown to be
fully stereospecific in the case of housanes when an enantiopure epoxide
was employed, leading to a streamlined access to highly valuable optically
active strain-release reagents.