title: Catalytic enantioselective synthesis of tetrahydroisoquinolines and their analogues bearing a C4 stereocenter: formal synthesis of (+)-(8S,13R)-cyclocelabenzine.
abstract: A one-pot wonder: 1,2,3,4-Tetrahydroisoquinolines with a C4 stereocenter can be formed by using a one-pot multicomponent chiral phosphoric acid catalyzed transformation of a mixture of oxetane-tethered benzaldehydes, amines, and the dimethyl ester derivative of the Hantzsch ester (see scheme). This transformation can be used to prepare the spermidine alkaloid (+)-(8S,13R)-cyclocelabenzine.
authors.affiliation: Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR, China.
authors.forename: Zhilong
authors.initials: Z
authors.lastname: Chen
authors.forename: Zhaobin
authors.initials: Z
authors.lastname: Wang
authors.forename: Jianwei
authors.initials: J
authors.lastname: Sun
mesh_terms: D000588:Amines / Q000737:chemistry; D001547:Benzaldehydes / Q000737:chemistry; D002384:Catalysis; D004952:Esters; D000077489:Piperazine; D010879:Piperazines / Q000737:chemistry; D013095:Spermidine / Q000031:analogs & derivatives; D013237:Stereoisomerism; D044005:Tetrahydroisoquinolines / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: C587308:(8S,13R)-cyclocelabenzine; D000588:Amines; D001547:Benzaldehydes; D004952:Esters; D010879:Piperazines; D044005:Tetrahydroisoquinolines; D000077489:Piperazine; D013095:Spermidine