NMR determination of the absolute configuration of cyclic chiral alkenes

Article abstract of DOI:10.1016/S0040-4039(98)02342-9

By the use of a new axially chiral reagent, 2'-methoxy-1,1'- binaphthalene-2-carbohydroximoyl chloride (MBCC), chiral cyclic alkenes were stereoselectively derivatized into 4,5-dihydroisoxazoles. NOEs were observed between the protons of the reagent moiety and those of the alkene moiety in cycloadducts. The absolute configuration of the original alkenes was unambiguously determined by the NOE correlation.