Catalytic enantioselective aza-Reformatsky reaction with seven-membered cyclic imines dibenzo[b, f][1, 4]oxazepines. Issue 8 (30th May 2017)

• Record Type: Journal Article
• Authors: De Munck, Lode; Sukowski, Verena; Vila, Carlos; Muñoz, M. Carmen; Pedro, José R.
• Is Part Of: Organic chemistry frontiers. Volume 4:Issue 8(2017)
• Page Start: 1624
• Page End: 1628
• Publication Date: 2017-05-30
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/c7qo00329c
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : A catalytic enantioselective aza-Reformatsky reaction with cyclic dibenzo[ b, f ][1, 4]oxazepines and ethyl iodoacetate is reported. Abstract : A catalytic enantioselective aza-Reformatsky reaction is reported with cyclic dibenzo[ b, f ][1, 4]oxazepines and ethyl iodoacetate leading to the synthesis of chiral ethyl 2-(10, 11-dihydrodibenzo[ b, f ][1, 4]oxazepin-11-yl)acetate derivatives with excellent yields and high enantioselectivities (up to 98% yield and 97 : 3 er) using a readily available diaryl prolinolL4 as the chiral ligand and Me2 Zn as the zinc source under an air atmosphere. Furthermore, different transformations were carried out with the corresponding chiral β-amino esters, preserving in all cases the optical purity.