Asymmetric ring-opening reaction of meso-epoxides with aromatic amines using homochiral metal-organic frameworks as recyclable heterogeneous catalysts.

ABSTRACT

An efficient asymmetric ring-opening (ARO) reaction of meso-epoxides with aromatic amines catalysed by a series of homochiral metal-organic frameworks (MOFs) was carried out. Excellent results (up to 95% ee) for the ARO of cyclohexene oxide with several aromatic amines were achieved with a homochiral MOF derived from the ligand (R)-2,2'-dihydroxyl-1,1'-binaphthalene-5,5'-dicarboxylic acid. Furthermore, homochiral MOFs based on (R)-2,2'-dihydroxy-1,1'-binaphthyl-4,4'-di(4-benzoic acid) and (R)-2,2'-diethoxy-1,1'-binaphthyl-4,4'-di(5-isophthalic acid) catalysed ARO reactions of cis-stilbene oxide with 1-naphthylamine in high yield (up to 95%) and excellent enantioselectivity (up to 97%) of the ß-amino alcohol. The MOF catalysts were recoverable and recyclable with retention of their performance.