Optical resolution and chiral synthesis of methyl 6,7-dichloro-2,3-dihydrobenzo(b)furan-2-carboxylate

Autor:	Yoshihiro Matsushita, Hiroshi Harada, Eiichi Ohsugi, Mitsuaki Yodo
Rok vydání:	1988
Předmět:	chemistry.chemical_classification Resolution (mass spectrometry) Chemistry Phenyl sulfide Carboxylic acid Enantioselective synthesis Furan-2-carboxylate General Chemistry General Medicine Combinatorial chemistry Chiral resolution Yield (chemistry) Drug Discovery Organic chemistry Enantiomer
Zdroj:	Chemical and Pharmaceutical Bulletin. 36:902-913
ISSN:	1347-5223 0009-2363
DOI:	10.1248/cpb.36.902
Popis:	Optical isomers of methyl 6, 7-dichloro-2, 3-dihydrobenzo[b]furan-2-carboxylate (2) were prepared by means of both optical resolution and chiral synthesis. The resolution of the carboxylic acid 3 was achieved in a practical and efficient way via the l-and d-menthyl esters, which were directly converted to enantiomers of 2. Chiral synthesis of 2 was attained with high optical yield via acidcatalyzed cyclization of the β-hydroxysulfide 10 derived from optically active glycidyl phenyl sulfide 13. The optical resolution method was considered to be better for large-scale preparation from the economical and operational viewpoints.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::4fbbe445413e50e9cafd71ad100b3fa4 https://doi.org/10.1248/cpb.36.902 Zobrazit plný text záznamu