Enantioselective syntheses of β-amino alcohols catalyzed by recyclable chiral Fe() metal complex

• Published in: RSC advances 2016-01, Vol.6 (9), p.7693-77
• Main Authors: Tak, Rajkumar, Kumar, Manish, Kureshy, Rukhsana I, Choudhary, Manoj Kumar, Khan, Noor-ul H, Abdi, Sayed H. R, Bajaj, Hari C
• Format: Article
• Language: English
• Subjects: Alcohols; Aniline; Asymmetry; Catalysts; Chlorides; Coordination compounds; Iron; Ligands
• ISSN: 2046-2069; 2046-2069
• DOI: 10.1039/c5ra23600b

An efficient asymmetric desymmetrization of meso -epoxides with anilines catalysed by a series of simple and environmentally benign in situ generated Fe( iii ) complexes based on chiral tridentate ligands L 1 -L 7 with achiral and chiral linkers (methylene, piperazine, R / S BINOL and diethyl tartrate) was carried out at rt. The in situ generated iron metal complex based on ligand L 5 a emerged as improved (low catalyst loading) catalyst for asymmetric desymmetrization of meso -epoxides with anilines giving high enantioselectivity (up to 99%) and high yield (95%) of enantiopure β-amino alcohols in 14 h. While excellent results for ARO of cyclic as well as aliphatic epoxides with anilines was achieved with in situ generated complex from the ligand L 4 h and Fe( iii ) chloride, the catalyst was recoverable and recyclable (five times) with retention of its performance. An efficient asymmetric desymmetrization of meso -epoxides with anilines catalyzed by a series of simple and environmentally benign in situ generated Fe( iii ) complexes based on chiral tridentate ligands L 1 -L 7 was carried out at rt.