An inherently chiral calix[4]crown carboxylic acid in the 1,2-alternate conformation

Autor:	Min Zhang, Yu-Xiang Xia, Guang-Ya Xiang, Si-Zhe Li, Jun Luo, Jiao Shi, Hao-Hui Zhou
Rok vydání:	2012
Předmět:	chemistry.chemical_classification Chiral auxiliary Stereochemistry Carboxylic acid Diastereomer General Chemistry Condensed Matter Physics Chiral resolution chemistry.chemical_compound Enantiopure drug chemistry Calixarene Chiral derivatizing agent Conformational isomerism Food Science
Zdroj:	Journal of Inclusion Phenomena and Macrocyclic Chemistry. 74:277-284
ISSN:	1573-1111 0923-0750
DOI:	10.1007/s10847-012-0111-2
Popis:	For better understanding of the structure/property relationship of inherently chiral calixarenes in the 1,2-alternate conformation, we designed and synthesized an inherently chiral calix[4]crown-4 carboxylic acid 1,2-alternate conformer. Resolution of the racemates was effected by condensation with (S)-BINOL as a chiral auxiliary and separation of the resultant diastereomers via preparative TLC plates, followed by hydrolysis of the isolated diastereomers to afford enantiopure antipodes of the title compound. Preliminary property study revealed that the title compound has the ability to enantioselectively discriminate 2-phenylglycinol by 1H NMR spectroscopy.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::afd948377d73bc0bee9922f7c3dd33d0 https://doi.org/10.1007/s10847-012-0111-2 Zobrazit plný text záznamu Full text from SpringerLink