Synthesis and Characterization of Acylated Chiral Oxazolidine-2-selones: Selone Chiral Derivatizing Agents for the Detection and Quantitation of Remotely Disposed Chiral Centers

Autor:	Mary E. Barr, Lukasz Lebioda, David A. Ashburn, Albert R. Garber, Rodolfo A. Martinez, R. Bruce Dunlap, Louis A. Silks, Jerome D. Odom, Jie Peng
Rok vydání:	1995
Předmět:	Oxazolidine organic chemicals Organic Chemistry Diastereomer Orbital overlap Nuclear magnetic resonance spectroscopy Highly sensitive Adduct chemistry.chemical_compound Crystallography chemistry heterocyclic compounds Enantiomer Selone
Zdroj:	The Journal of Organic Chemistry. 60:5540-5549
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo00122a039
Popis:	Racemic and chiral carboxylic acids and acid chlorides are coupled cleanly to oxazolidine-2-selone chiral derivatizing agents (CDA`s) with yields ranging from 85 to 99%. {sup 77}Se NMR spectroscopy provides a highly sensitive method for the determination of the enantiomeric excesses of these remotely disposed chiral centers. The geometrical relationship between the selenocarbonyl and the adduct carbonyl (syn or anti) appears to have a profound effect on the chemical shift difference ({Delta}{delta}{sub Se}) observed for pairs of adduct diastereomers. Crystallographic and solution state NMR studies suggest that the syn orbital overlap enhances the {Delta}{delta}{sub Se}. 12 figs., 8 tabs.
Databáze:	OpenAIRE
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