Synthesis and Optical Resolution of Configurationally Stable Zwitterionic Pentacoordinate Silicon Derivatives - Sorbonne Université
Journal Articles Angewandte Chemie International Edition Year : 2022

Synthesis and Optical Resolution of Configurationally Stable Zwitterionic Pentacoordinate Silicon Derivatives

Abstract

Stereogenic silicon centres in functionalized tetracoordinated organosilanes generally exhibit very high configurational stability under neutral conditions. This stability drops completely when higher coordination states of the silicon center are reached due to rapid substituent exchange. Herein we describe the synthesis of chiral and neutral pentacoordinate silicon derivatives with high configurational stability. The zwitterionic nature of these air and water tolerant species allows for the first time their direct and efficient optical resolution using chiral HPLC techniques. By means of this method, pentacoordinate silicon compounds exhibiting high Si-inversion have been obtained as single enantiomers. A rationalisation of the enantiomerisation pathways has been also carried out using DFT calculations.
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Dates and versions

hal-03440769 , version 1 (22-11-2021)

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Thomas Deis, Julien Maury, Fabrizio Medici, Marion Jean, Jérémy Forte, et al.. Synthesis and Optical Resolution of Configurationally Stable Zwitterionic Pentacoordinate Silicon Derivatives. Angewandte Chemie International Edition, 2022, 61 (3), pp.e202113836. ⟨10.1002/anie.202113836⟩. ⟨hal-03440769⟩
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