Chalcogen-based chiral reagents for nuclear magnetic resonance d

Details Chalcogen-based chiral reagents for nuclear magnetic resonance d Chalcogen-based chiral reagents for nuclear magnetic resonance d

1993-03-05

1994-09-06

Daus, Donald G.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548230, 436173, C07D26316

Patent

active

053449363

ABSTRACT:
Selenium reagents when coupled to a compound containing an asymmetric carbon atom can be used in a highly sensitive method for determination of enantiomeric purity and for stereochemical assignment. Preferred reagents include a selenocarbonyl moiety (Se=C) and a reactive center for coupling to the compound of interest. Particularly preferred selenocarbonyls for use in the invention are chiral selenooxazolidinones of the formula ##STR1## wherein R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are selected from among hydrogen, alkyl of up to 10 carbons and aryl having up to 12 carbon atoms in the ring system. The substituent R.sup.1 is selected to facilitate the formation of a bond between the nitrogen atom of the selenooxazolidinone reagent and the compound of interest. Since the ability of the reagent to resolve enantiomers decreases as the number of bonds between the selenium and the asymmetric carbon increases, the reactive center is preferably located no more than three bonds from the selenium atom.

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