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Organocatalytic Amination of Pyrazolones with Azodicarboxylates: Scope and Limitations
Author(s) -
Formánek Bedřich,
Šeferna Vít,
Meazza Marta,
Rios Ramon,
Patil Mahendra,
Veselý Jan
Publication year - 2021
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.202100167
Subject(s) - chemistry , amination , pyrazolones , stereocenter , hydrazine (antidepressant) , adduct , catalysis , organic chemistry , organocatalysis , cinchona , enantioselective synthesis , combinatorial chemistry , chromatography
The organocatalytic amination of pyrazol‐5‐ones with azodicarboxylates (catalyzed by quinine) is reported. This asymmetric process furnishes enantiomerically enriched hydrazine adducts containing quaternary stereocenters in high yields (74–96 %) and enantioselectivities (up to ee 97 %). Theoretical calculations allow us to propose the relations between quinine catalyst and reactants leading to observed stereochemical outcome and trends in the effectivity of the reaction.