An asymmetric three-component reaction of a diazo compound with an alcohol and a seven-membered imine. Issue 8 (7th March 2022)

• Record Type: Journal Article
• Authors: Xie, Xiongda; Bao, Ming; Chen, Kewei; Xu, Xinfang; Hu, Wenhao
• Is Part Of: Organic chemistry frontiers. Volume 9:Issue 8(2022)
• Page Start: 2102
• Page End: 2108
• Publication Date: 2022-03-07
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d2qo00076h
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : An asymmetric three-component reaction via Mannich-type interception of an oxonium ylide with a 7-membered imine has been disclosed, providing chiral dibenzoazepine analogues with excellent stereoselectivity and structural diversity. Abstract : A dirhodium and chiral phosphoric acid co-catalyzed asymmetric three-component reaction of a diazo compound with an alcohol and a seven-membered imine has been developed via Mannich-type interception of a transient oxonium ylide. This reaction provides an efficient approach for the synthesis of chiral dibenzoazepine analogues, including dibenzo[ b, f ][1, 4]oxazepine, dibenzo[ b, f ][1, 4]thiazepine, and dibenzo[ b, e ]azepine derivatives, in generally good yields with excellent stereoselectivity (91%–99% ee) under mild reaction conditions. This reaction shows broad substrate generality, and these generated products could be further converted to enantioenriched tetracyclic frameworks with embedded functional groups.