Synthesis of Optically Pure 3,3′-Disubstituted-1,1′-Bi-6-Methoxy-2-Phenol (BIPhOL) Derivatives via Diastereomeric Resolution

Autor:	Chun Young Lee, Jung Min Yoon, Young In Jo, Cheol Hong Cheon
Rok vydání:	2016
Předmět:	Diastereomeric recrystallization 010405 organic chemistry Stereochemistry Aryl Organic Chemistry Diastereomer Enantioselective synthesis 010402 general chemistry 01 natural sciences Chiral resolution Coupling reaction 0104 chemical sciences chemistry.chemical_compound chemistry Moiety Boronic acid
Zdroj:	The Journal of Organic Chemistry. 81:8464-8469
ISSN:	1520-6904 0022-3263
DOI:	10.1021/acs.joc.6b01645
Popis:	A new protocol for the enantioselective synthesis of 3,3'-disubstituted-1,1'-bi-6-methoxy-2-phenol (BIPhOL) derivatives is described. Diastereomeric resolution of racemic BIPhOL boronic acid using a boronic acid moiety as a resolving group generated two diastereomers and subsequent Suzuki-Miyaura coupling reaction of the resulting diastereomers with aryl halides provided BIPhOL derivatives without any loss of enantioselectivity. In addition, the absolute stereochemistry of chiral BIPhOL was determined by comparison of the optical rotation with the reported value.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::cae64ab1932ef7ddf6cc2a00e10a33d5 https://doi.org/10.1021/acs.joc.6b01645 Zobrazit plný text záznamu