Chiral 2,2-disubstituted cyclopropanecarboxylic acids: Effective derivatizing agents for analysis of enantiomeric purity of alcohols and for resolution of 1,1'-bi-2-naphthol

Abstract

The enantiomeric purities of secondary alcohols can be easily analyzed by GC and HPLC through derivatization to the esters of 2,2-disubstituted cyclopropanecarboxylic acids 1, and by H-1 NMR analysis of the esters of 2,2-diphenylcyclopropanecarboxylic acid (Ib). In addition racemic 1,1'-bi-2-naphthol is easily resolved through derivatization to monoesters of 2,2-dimethy]cyclopropanecarboxylic acid (1a), which are crystallized selectively and sequentially in high yields with high optical purities. (C) 1997 Elsevier Science Ltd.