Spirocyclic zwitterionic, lambda Si-5-silicates with two bidentate ligands derived from alpha-amino acids or alpha-hydroxycarboxylic acids: Synthesis, structure, and stereodynamics

A series of zwitterionic lambda(5)Si-silicates with a (2,2,6,6-tetramethylpiperidinio)methyl group and two identical bidentate ligands derived from glycine, (S)-alanine, (S)-phenylalanine, glycolic acid, (S)-lactic acid, (S)-3-phenyl lactic acid, or (S)-mandelic acid were synthesized and structurall...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 126; no. 44; pp. 14493 - 14505
Main Authors Tacke, R, Bertermann, R, Burschka, C, Dragota, S, Penka, M, Richter
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 10.11.2004
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
SILICATES
CRYSTAL-STRUCTURE ANALYSES
BEHAVIOR
PENTACOORDINATE SILICON-COMPOUNDS
HYDRATE
DYNAMIC STEREOCHEMISTRY
SOLID-STATE
ELECTRONIC-STRUCTURE
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Summary:A series of zwitterionic lambda(5)Si-silicates with a (2,2,6,6-tetramethylpiperidinio)methyl group and two identical bidentate ligands derived from glycine, (S)-alanine, (S)-phenylalanine, glycolic acid, (S)-lactic acid, (S)-3-phenyl lactic acid, or (S)-mandelic acid were synthesized and structurally characterized (solution and solid-state NMR spectroscopy; single-crystal X-ray diffraction). The chiral lambda(5)Si-licates with ligands derived from optically active a.-amino acids or (alpha-hydroxycarboxylic acids were isolated as enantiomerically and diastereomerically pure compounds that undergo a (Delta)/(Delta)-epimerization in solution.
ISSN:0002-7863
DOI:10.1021/ja047248z