Evans Enolates: Solution Structures of Lithiated Oxazolidinone-Derived Enolates

The results of a combination of 6Li and 13C NMR spectroscopic and computational studies of oxazolidinone-based lithium enolatesEvans enolatesin tetrahydrofuran (THF) solution revealed a mixture of dimers, tetramers, and oligomers (possibly ladders). The distribution depended on the structure of th...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2015-10, Vol.137 (40), p.13087-13095
Main Authors: Tallmadge, Evan H, Collum, David B
Format: Article
Language:English
Subjects:
Dimerization
Lithium - chemistry
Magnetic Resonance Spectroscopy
Molecular Structure
Oxazolidinones - chemistry
Solutions
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Summary:The results of a combination of 6Li and 13C NMR spectroscopic and computational studies of oxazolidinone-based lithium enolatesEvans enolatesin tetrahydrofuran (THF) solution revealed a mixture of dimers, tetramers, and oligomers (possibly ladders). The distribution depended on the structure of the oxazolidinone auxiliary, substituent on the enolate, and THF concentration (in THF/toluene mixtures). The unsolvated tetrameric form contained a D 2d -symmetric core structure, whereas the dimers were determined experimentally and computationally to be trisolvates with several isomeric forms.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.5b08207