title: A novel Lewis acid catalyzed [3 + 3]-annulation strategy for the syntheses of tetrahydro-β-carbolines and tetrahydroisoquinolines.
abstract: A novel Lewis acid catalyzed [3 + 3]-annulation process for the efficient syntheses of both tetrahydro-β-carbolines and tetrahydroisoquinolines from readily available benzylic alcohols and aziridines was developed, which would be a highly valuable complement to the widely used Pictet-Spengler reaction. A probable mechanism was proposed based on the isolation and characterization of two key intermediates. This strategy enables facile access to important alkaloid frameworks not easily available with other known methods.
authors.affiliation: Laboratory of Functionalized Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials, Institute of Organic Chemistry, School of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui 241000, PR China.
authors.forename: Shaoyin
authors.initials: S
authors.lastname: Wang
authors.forename: Zhuo
authors.initials: Z
authors.lastname: Chai
authors.forename: Shuangliu
authors.initials: S
authors.lastname: Zhou
authors.forename: Shaowu
authors.initials: S
authors.lastname: Wang
authors.forename: Xiancui
authors.initials: X
authors.lastname: Zhu
authors.forename: Yun
authors.initials: Y
authors.lastname: Wei
mesh_terms: D000470:Alkaloids / Q000737:chemistry*; D002243:Carbolines / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D058116:Lewis Acids / Q000737:chemistry*; D015394:Molecular Structure; D044005:Tetrahydroisoquinolines / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D000470:Alkaloids; D002243:Carbolines; D058116:Lewis Acids; D044005:Tetrahydroisoquinolines