title: One-pot stereoselective synthesis of α,β-differentiated diamino esters via the sequence of aminochlorination, aziridination and intermolecular SN2 reaction.
abstract: We report here an efficient one-pot method for the synthesis of α,β-differentiated diamino esters directly from cinnamate esters using N,N-dichloro-p-toluenesulfonamide and benzylamine as nitrogen sources. The key transformations include a Cu-catalyzed aminohalogenation and aziridination, followed by an intermolecular SN2 nucleophilic ring opening by benzylamine. The reactions feature a wide scope of substrates and proceed with excellent stereo- and regioselectivity (anti:syn >99:1) .
authors.affiliation: School of Chemsitry and Chemical Engineering, State of Key Laboratory of Coordination, Nanjing University, Nanjing, 210093, China.
authors.forename: Yiwen
authors.initials: Y
authors.lastname: Xiong
authors.affiliation: School of Chemsitry and Chemical Engineering, State of Key Laboratory of Coordination, Nanjing University, Nanjing, 210093, China.
authors.forename: Ping
authors.initials: P
authors.lastname: Qian
authors.affiliation: School of Chemsitry and Chemical Engineering, State of Key Laboratory of Coordination, Nanjing University, Nanjing, 210093, China.
authors.forename: Chenhui
authors.initials: C
authors.lastname: Cao
authors.affiliation: School of Chemsitry and Chemical Engineering, State of Key Laboratory of Coordination, Nanjing University, Nanjing, 210093, China.
authors.forename: Haibo
authors.initials: H
authors.lastname: Mei
authors.affiliation: School of Chemsitry and Chemical Engineering, State of Key Laboratory of Coordination, Nanjing University, Nanjing, 210093, China ; Institute for Chemistry & BioMedical Sciences, Nanjing University, Nanjing, 210093, China ; High-Tech Research Institute of Nanjing University, Changzhou, 213164, China.
authors.forename: Jianlin
authors.initials: J
authors.lastname: Han
authors.affiliation: Institute for Chemistry & BioMedical Sciences, Nanjing University, Nanjing, 210093, China ; Department of Chemsitry and Biochemistry, Texas Tech Unviersity, Lubbock, Texas, 79409-1061, USA.
authors.forename: Guigen
authors.initials: G
authors.lastname: Li
authors.affiliation: School of Chemsitry and Chemical Engineering, State of Key Laboratory of Coordination, Nanjing University, Nanjing, 210093, China.
authors.forename: Yi
authors.initials: Y
authors.lastname: Pan
keywords: aminohalogenation; diamination; one-pot; stereoselectivity; α,β-diamino ester