ja5b00861_si_003.cif (20.18 kB)
Stereocontrol in Nucleophilic Substitution Reactions at Silicon: The Role of Permutation in Generating Silicon-Centered Chirality
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posted on 2015-04-08, 00:00 authored by Jonathan O. Bauer, Carsten StrohmannIntramolecular isomerization in pentacoordinate
compounds can play
an essential role for the adjustment of defined stereochemical information.
Here, we present a conclusive mechanism of a stereocontrolled reaction
on chiral dimethoxysilanes that opens new aspects in understanding
the origin of creating silicon-centered chirality during a nucleophilic
substitution process. By combining experimental, structural, and quantum
chemical methods, we were able to disclose an interconversion process,
based on consecutive Berry-type motions, as the most plausible mechanism
for describing the stereochemical outcome in suchlike substitution
reactions.
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originsuchlike substitution reactionsstereochemical outcomePermutationquantum chemical methodsRoleaspectGeneratinginterconversion processchiralitymechanismrolestereocontrolled reactionStereocontrolChiralityIntramolecularunderstandingSiliconstereochemical informationpentacoordinate compoundsnucleophilic substitution processisomerizationNucleophilic Substitution Reactionschiral dimethoxysilanes
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