title: Copper(II)/amine synergistically catalyzed enantioselective alkylation of cyclic N-acyl hemiaminals with aldehydes.
abstract: The first catalytic asymmetric alkylation of N-acyl quinoliniums with aldehydes has been described. A copper/amine synergistic catalytic system has been developed, allowing the addition of functionalized aldehydes to a wide range of electronically varied N-acyl quinoliniums in good yields with excellent enantiocontrol. The synergistic catalytic system was also effective for N-acyl dihydroisoquinoliniums and β-caboliniums, demonstrating the general applicability of the protocol in the enantioselective alkylation of diverse cyclic N-acyl hemiaminals.
authors.affiliation: Key Lab of Chemical Biology of Ministry Education, School of Pharmaceutical Sciences, Jinan 250012, China. leiliu@sdu.edu.cn.
authors.forename: Shutao
authors.initials: S
authors.lastname: Sun
authors.forename: Ying
authors.initials: Y
authors.lastname: Mao
authors.forename: Hongxiang
authors.initials: H
authors.lastname: Lou
authors.forename: Lei
authors.initials: L
authors.lastname: Liu
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000478:Alkylation; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D008698:Mesylates / Q000737:chemistry; D011804:Quinolines / Q000737:chemistry; D011806:Quinolinium Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000588:Amines; D008698:Mesylates; D011804:Quinolines; D011806:Quinolinium Compounds; D003300:Copper; C037219:quinoline; C012077:trifluoromethanesulfonic acid