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Regioconvergent and Enantioselective Rhodium‐Catalyzed Hydroamination of Internal and Terminal Alkynes: A Highly Flexible Access to Chiral Pyrazoles
Author(s) -
Haydl Alexander M.,
Hilpert Lukas J.,
Breit Bernhard
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201601198
Subject(s) - enantiopure drug , enantioselective synthesis , rhodium , hydroamination , pyrazole , allylic rearrangement , chemistry , combinatorial chemistry , catalysis , substrate (aquarium) , regioselectivity , terminal (telecommunication) , stereochemistry , organic chemistry , computer science , telecommunications , oceanography , geology
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.