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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

✍ Scribed by Hyun Chang Kim; Soojin Choi; Hongdoo Kim; Kwang-Hyun Ahn; Jeong Hwan Koh; Jaiwook Park

Book ID: 104257151
Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 190 KB
Volume: 38
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(97)00789-2

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✦ Synopsis

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 NMR analysis of the esters of 2,2-diphenylcyclopropanecarboxylic acid (Ib). In addition racemic l,l'-bi-2-naphthol is easily resolved through derivatization to monoesters of 2,2-dimethylcyclopropanecarboxylic acid (la), which are crystallized selectively and sequentially in high yields with high optical purities.

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