Premium
Asymmetric Addition of Pyrazolones to Allenamides Catalyzed by a Chiral Phosphoric Acid
Author(s) -
Yang Kai,
Bao Xiaoze,
Liu Siyuan,
Xu Jingnan,
Qu Jingping,
Wang Baomin
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201801039
Subject(s) - pyrazolones , stereocenter , chemistry , allylic rearrangement , enantioselective synthesis , pyrazolone , phosphoric acid , squaramide , catalysis , chirality (physics) , tsuji–trost reaction , organic chemistry , organocatalysis , combinatorial chemistry , chiral symmetry breaking , physics , quark , nambu–jona lasinio model , quantum mechanics
We describe a new asymmetric allylic alkylation of pyrazolones, in which an all‐carbon quaternary stereocenter with broad substrate scope and good enantioselectivity was generated. The asymmetric addition of pyrazolones to allenamides could be carried out under mild conditions in excellent yields with a relatively low catalyst loading. The allylic products with an enamide structure can be easily transformed to the pyrazolones with other functional groups, which provides a new approach for the asymmetric introduction of new functional groups into the pyrazolone skeleton.