Stereospecific Construction of Quaternary Carbon Stereocenters from Quaternary Carbon Stereocenters

Kaushalendra Patel; Veeranjaneyulu Lanke; Ilan Marek

doi:10.1021/jacs.2c01695

Stereospecific Construction of Quaternary Carbon Stereocenters from Quaternary Carbon Stereocenters

Kaushalendra Patel, Veeranjaneyulu Lanke, Ilan Marek

Chemistry

Technion - Israel Institute of Technology

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	7066-7071
Number of pages	6
Journal	Journal of the American Chemical Society
Volume	144
Issue number	16
DOIs	https://doi.org/10.1021/jacs.2c01695
State	Published - 27 Apr 2022

Keywords

Carbon
Catalysis
Molecular Structure
Stereoisomerism

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10.1021/jacs.2c01695

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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.",

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N2 - 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.

AB - 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.

KW - Carbon

KW - Catalysis

KW - Molecular Structure

KW - Stereoisomerism

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Stereospecific Construction of Quaternary Carbon Stereocenters from Quaternary Carbon Stereocenters

Abstract

Keywords

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