title: Regioconvergent and Enantioselective Rhodium-Catalyzed Hydroamination of Internal and Terminal Alkynes: A Highly Flexible Access to Chiral Pyrazoles.
abstract: The rhodium-catalyzed asymmetric N-selective coupling of pyrazole derivatives with internal and terminal alkynes features an utmost chemo-, regio-, and enantioselective access to enantiopure allylic pyrazoles, readily available for incorporation in small-molecule pharmaceuticals. This methodology is distinguished by a broad substrate scope, resulting in a remarkable compatability with a variety of different functional groups. It furthermore exhibits an intriguing case of regio-, position-, and enantioselectivity in just one step, underscoring the sole synthesis of just one out of up to six possible products in a highly flexible approach to allylated pyrazoles by emanating from various internal and terminal alkynes.
authors.affiliation: Institut für Organische Chemie, Albert-Ludwigs-Universität Freiburg, Albertstrasse 21, 79104, Freiburg im Breisgau, Germany.
authors.forename: Alexander M
authors.initials: AM
authors.lastname: Haydl
authors.affiliation: Institut für Organische Chemie, Albert-Ludwigs-Universität Freiburg, Albertstrasse 21, 79104, Freiburg im Breisgau, Germany.
authors.forename: Lukas J
authors.initials: LJ
authors.lastname: Hilpert
authors.affiliation: Institut für Organische Chemie, Albert-Ludwigs-Universität Freiburg, Albertstrasse 21, 79104, Freiburg im Breisgau, Germany. bernhard.breit@chemie.uni-freiburg.de.
authors.forename: Bernhard
authors.initials: B
authors.lastname: Breit
mesh_terms: D000480:Alkynes / Q000138:chemical synthesis* / Q000737:chemistry*; D000586:Amination; D002384:Catalysis; D015394:Molecular Structure; D011720:Pyrazoles / Q000138:chemical synthesis* / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D011720:Pyrazoles; D012238:Rhodium
keywords: alkynes; allylic compounds; asymmetric catalysis; heterocycles; rhodium