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From Palladium to Brønsted Acid Catalysis: Highly Enantioselective Regiodivergent Addition of Alkoxyallenes to Pyrazolones
Author(s) -
Zhou Hui,
Wei Zhao,
Zhang Jinlong,
Yang Huameng,
Xia Chungu,
Jiang Gaoxi
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201610473
Subject(s) - pyrazolones , stereocenter , enantioselective synthesis , tsuji–trost reaction , allylic rearrangement , palladium , pyrazolone , chemistry , catalysis , brønsted–lowry acid–base theory , combinatorial chemistry , organic chemistry
Abstract A highly enantioselective regiodivergent addition of alkoxyallenes to pyrazolones was developed to afford multiply functionalized alkylated products bearing a quaternary carbon stereocenter in high yields with excellent stereoselectivities. One approach is enabled by palladium catalysis, thus leading to branched allylic pyrazol‐5‐ones under mild reaction conditions. The other is catalyzed by a chiral Brønsted acid to give linear products exclusively. Moreover, the usefulness of this new method was highlighted by converting the allylic products into other interesting multifunctionalized pyrazolone derivatives which would be of great potential for the exploitation of pharmaceutically important molecules.