108940-99-4Relevant academic research and scientific papers
Optical Resolution and Chiral Synthesis of Methyl 6,7-Dichloro-2,3-dihydrobenzofuran-2-carboxylate
Yodo, Mitsuaki,Matsushita, Yoshihiro,Ohsugi, Eiichi,Harada, Hiroshi
, p. 902 - 913 (2007/10/02)
Optical isomers of methyl 6,7-dichloro-2,3-dibenzofuran-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 acid-catalyzed 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.Keywords - methyl 6,7-dichloro-2,3-dibenzofuran-2-carboxylate; optical resolution; (R)-4-phenyl-2-oxazolidone; menthol; chiral synthesis; glycidyl phenyl sulfide; β-hydroxysulfide; episulfonium ion; S-8666
