Literature DB >> 26437278

Evans Enolates: Solution Structures of Lithiated Oxazolidinone-Derived Enolates.

Evan H Tallmadge1, David B Collum1.   

Abstract

The results of a combination of (6)Li and (13)C 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.

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Year:  2015        PMID: 26437278      PMCID: PMC4765922          DOI: 10.1021/jacs.5b08207

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


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