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Stereospecific Construction of Quaternary Carbon Stereocenters from Quaternary Carbon Stereocenters.

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.

SUBMITTER: Patel K

PROVIDER: S-EPMC9052742 | biostudies-literature | 2022 Apr

REPOSITORIES: biostudies-literature

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Stereospecific Construction of Quaternary Carbon Stereocenters from Quaternary Carbon Stereocenters.

Patel Kaushalendra K Lanke Veeranjaneyulu V Marek Ilan I

Journal of the American Chemical Society 20220412 16

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. ...[more]

PMID: 35412821

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