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Stereospecific Construction of Quaternary Carbon Stereocenters from Quaternary Carbon Stereocenters

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Organoaluminum species promote a smooth nucleophilic substitution at the quaternary carbon stereocenter of stereodefined polysubstituted cyclopropyl methyl phosphate with a complete inversion of configuration, even when more reactive functional groups… Click to show full abstract

Organoaluminum species promote a smooth nucleophilic substitution at the quaternary carbon stereocenter of stereodefined polysubstituted cyclopropyl methyl phosphate with a complete inversion of configuration, even when more reactive functional groups are present. The regio- and diastereoselectivity of the substitution is attributed to the existence of a bicyclobutonium intermediate.

Keywords: carbon; quaternary carbon; carbon stereocenters; stereocenters quaternary; construction quaternary; stereospecific construction

Journal Title: Journal of the American Chemical Society
Year Published: 2022

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