Tetrahedron letters

A convenient family of chiral shift reagents for measurement of enantiomeric excesses of sulfoxides

M Deshmukh, E Dunach, S Juge, HB Kagan

Index: Deshmukh, M.; Dunnach, E.; Juge, S.; Kagan, H. B. Tetrahedron Letters, 1984 , vol. 25, # 32 p. 3467 - 3470

Full Text: HTML

Citation Number: 108

Abstract

Abstract (R)(−)-N-(3, 5-dinitrobenzoyl)-α-phenylethylamine is a good chiral shift reagent for sulfoxides such as Ar-(SO)-CH 3 (Ar= substituted phenyl, naphthyl) or R-(SO)-CH 3 (R= t-Bu, Cyclohexyl, n-Octyl). 1-Naphthyl propyl sulfoxide was also successfully resolved. The sharpness of the signals allows to measure ee's in the range of 90%. Twenty-five examples are given.