DIRECT CHIRALITY DETERMINATION OF SECONDARY CARBINOL BY CHIRALITY RECOGNITION ABILITY OF C2 SYMMETRY 1,1'-BINAPHTHYL-2,2'-DIYL PHOSPHORYL CHLORIDE

The chirality of the secondary carbinol carbon atom can, directly and highly sensitively, be decided by derivation into a C2 symmetry 1,1 ’-binaphthyl-2,2’-diyl phosphate. The secondary carbinols and 1,1,-binaphthyl-2,2’-diyl phosphoryl chloride ((BNP)Cl) with the same chirality react preferentially over that with different chirality. The result is characteristically confirmed by the CD spectrum, since the intramolecular bonded naphthol-naphthol moiety causes a Davydov splitting with a very strong intensity. The chirality recognition ability of the BNP reagent is not affected by ring size, neighboring functional groups, or the configuration of the hydroxyl group in the alcohol compounds. And, the ability is exhibited with acyclic alcohols, as well as the cyclic compounds. The diastereomeric excess of the preferential pair can be calculated easily by the integrated area of the signals on the NMR spectrum. © 1990, American Chemical Society. All rights reserved.