title: Brønsted Acid Catalyzed Asymmetric Hydroamination of Alkenes: Synthesis of Pyrrolidines Bearing a Tetrasubstituted Carbon Stereocenter.
abstract: The first highly enantioselective Brønsted acid catalyzed intramolecular hydroamination of alkenes enables the efficient construction of a series of chiral (spirocyclic) pyrrolidines with an α-tetrasubstituted carbon stereocenter with excellent functional group tolerance. A unique feature of this strategy is the use of a thiourea group acting as both the activating and the directing group through cooperative multiple hydrogen bonding with a Brønsted acid and the double bond. The utility of this method is highlighted by the facile construction of chiral synthetic intermediates and important structural motifs that are widely found in organic synthesis.
authors.affiliation: Department of Chemistry, South University of Science and Technology of China, Shenzhen, 518055 (P. R. China).
authors.forename: Jin-Shun
authors.initials: JS
authors.lastname: Lin
authors.affiliation: Department of Chemistry, South University of Science and Technology of China, Shenzhen, 518055 (P. R. China).
authors.forename: Peng
authors.initials: P
authors.lastname: Yu
authors.affiliation: Department of Chemistry, South University of Science and Technology of China, Shenzhen, 518055 (P. R. China).
authors.forename: Lin
authors.initials: L
authors.lastname: Huang
authors.affiliation: Department of Chemistry, South University of Science and Technology of China, Shenzhen, 518055 (P. R. China).
authors.forename: Pan
authors.initials: P
authors.lastname: Zhang
authors.affiliation: Department of Chemistry, South University of Science and Technology of China, Shenzhen, 518055 (P. R. China). tanb@sustc.edu.cn.
authors.forename: Bin
authors.initials: B
authors.lastname: Tan
authors.affiliation: Department of Chemistry, South University of Science and Technology of China, Shenzhen, 518055 (P. R. China). liuxy3@sustc.edu.cn.
authors.forename: Xin-Yuan
authors.initials: XY
authors.lastname: Liu
mesh_terms: D000143:Acids / Q000737:chemistry; D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry*; D000586:Amination; D002244:Carbon / Q000737:chemistry; D002384:Catalysis; D060326:Chemistry Techniques, Synthetic; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000143:Acids; D000475:Alkenes; D011759:Pyrrolidines; D002244:Carbon
keywords: Brønsted acid catalysis; alkenes; asymmetric catalysis; hydroamination; pyrrolidines