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Palladium‐ and Rhodium‐Catalyzed Dynamic Kinetic Resolution of Racemic Internal Allenes Towards Chiral Pyrazoles
Author(s) -
Hilpert Lukas J.,
Sieger Simon V.,
Haydl Alexander M.,
Breit Bernhard
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201812984
Subject(s) - kinetic resolution , chemistry , alkene , rhodium , allene , racemization , palladium , catalysis , combinatorial chemistry , enantioselective synthesis , stereochemistry , organic chemistry
A complementing Pd‐ and Rh‐catalyzed dynamic kinetic resolution (DKR) of racemic allenes leading to N ‐allylated pyrazoles is described. Such compounds are of enormous interest in medicinal chemistry as certified drugs and potential drug candidates. The new methods feature high chemo‐, regio‐ and enantioselectivities aside from displaying a broad substrate scope and functional group compatibility. A mechanistic rational accounting for allene racemization and trans ‐alkene selectivity is discussed.