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Chiral Memory in Silylium Ions.

P Ducos1, V Liautard1, F Robert2

  • 1Institute of Molecular Sciences, UMR-CNRS 5255, University of Bordeaux 351, Cours de la libération 33405 Talence cedex (France).

Chemistry (Weinheim an Der Bergstrasse, Germany)
|July 4, 2015
PubMed
Summary

Chiral silicon centers in silylium ions exhibit stability with lone-pair interactions but lose configuration with π-interactions. The strength of Lewis base interaction dictates the transfer of chirality to the silicon center.

Keywords:
H transfercationschiralitysilylium ionsstereochemistry

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Area of Science:

  • Organosilicon chemistry
  • Stereochemistry
  • Lewis base adducts

Background:

  • Chiral silicon centers are crucial in stereoselective synthesis.
  • Understanding the stability of these centers is key to controlling stereochemical outcomes.
  • Lewis base-stabilized silylium ions present a unique system for studying chiral silicon stability.

Purpose of the Study:

  • To investigate the configurational stability of the chiral silicon center in Lewis base-stabilized silylium ions.
  • To determine the influence of different stabilization interactions (lone-pair vs. π-interactions) on stereochemical integrity.
  • To elucidate the conditions governing the transfer of axial chirality to silicon-centered chirality.

Main Methods:

  • Study of silylium ions stabilized by various Lewis bases.
  • Variable temperature studies to assess configurational stability.
  • Analysis of epimerization kinetics under different conditions, including solvent effects.
  • Evaluation of the relationship between Lewis base-silylium ion interaction strength and chirality transfer.

Main Results:

  • Complete retention of configuration at the chiral silicon center was observed at low temperatures for silylium ions stabilized by lone-pair interactions.
  • Loss of chiral memory (epimerization) occurred in systems stabilized by π-interactions.
  • Epimerization was facilitated by equilibration at room temperature or by the addition of catalytic amounts of chelating solvents.
  • The strength of the Lewis base-silylium ion interaction was identified as a critical factor for the successful transfer of axial chirality to silicon-centered chirality.

Conclusions:

  • The configurational stability of chiral silicon centers in Lewis base-stabilized silylium ions is highly dependent on the nature of the Lewis base interaction.
  • Lone-pair interactions provide robust stabilization, preserving silicon's chirality, whereas π-interactions lead to instability and epimerization.
  • Effective transfer of axial chirality to silicon requires a strong Lewis base-silylium ion interaction, highlighting the importance of adduct stability in stereochemical control.