Synthesis and characterization of acylated chiral oxazolidine-2-selones: Selone chiral derivatizing agents for the detection and quantitation of remotely disposed chiral centers

Journal Article · Fri Aug 25 00:00:00 EDT 1995 · Journal of Organic Chemistry

DOI:https://doi.org/10.1021/jo00122a039· OSTI ID:468729

Peng, Jie; Lebioda, L; Garber, A R; Odom, J D; Dunlap, R B ^[1]

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1. Los Alamos National Lab., NM (United States); and others

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.

• Sponsoring Organization: USDOE
• OSTI ID: 468729
• Journal Information: Journal of Organic Chemistry, Vol. 60, Issue 17; Other Information: PBD: 25 Aug 1995
• Country of Publication: United States
• Language: English

Related Subjects

40 CHEMISTRY
SELENIUM COMPOUNDS
CHEMICAL PREPARATION
NUCLEAR MAGNETIC RESONANCE
ORGANIC COMPOUNDS
STEREOCHEMISTRY
CHEMICAL REACTION YIELD
CHEMICAL SHIFT