The synthesis of cyclopropanes is of contemporary interest due to their ubiquity in small molecule pharmaceuticals and agrochemicals as well as their use as synthetic intermediates. There are currently a range of methods for the efficient synthesis of these carbocycles, however, many of these methods have difficulty in transferring an un-stabilized alkyl carbene unit. This is due to the instability and toxicity often associated with alkyl diazo compounds and a deleterious 1,2-hydride shift often observed in metal carbenoids with β-hydrogens. Herein we report a general method to transfer the alkyl and dialkyl carbene synthon via cyclopropanation with sulfone anions. In the presence of NaNH2, alkyl sulfones are able to cyclopropanate a range of styrenes (both benzenoid and heteroaromatic) in up to 84% isolated yield. We have synthesized a library of sulfones capable of transferring the 1,1’-dialkyl carbene group resulting in gem-dimethylcyclopropanes, spirocyclic compounds, and a number of other compounds containing alkyl cyclopropanes.

Efficient synthesis of orphaned cyclopropanes using sulfones as carbene synthons

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ACS Fall 2022

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