Cyclopropanone derivatives have long been considered unsustainable synthetic intermediates due to their important kinetic instability. In this work, we have achieved the first enantioselective synthesis of 1-sulfonylcyclopropanols, acting as stable yet powerful equivalents of the corresponding cyclopropanone derivatives under basic conditions. This method constitutes the first general approach to chiral, enantioenriched cyclopropanone derivatives. Both the electronic and steric nature of the sulfonyl moiety were found to have a crucial impact on their rate of equilibration to cyclopropanone, highlighting the modular reactivity of these reagents. Their utility is demonstrated in the development of a mild and stereospecific formal [3+1] cycloaddition with hydroxylamines as practical nitrenoid equivalents, leading to the efficient formation of chiral β-lactam derivatives.

Enantioselective synthesis of cyclopropanone equivalents and its application for the production of chiral β-lactams by formal [3+1] cycloaddition

ACS Fall 2020 Virtual Meeting

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