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Bifunctional Cinchona Alkaloid/Thiourea Catalyzes Direct and Enantioselective Vinylogous Michael Addition of 3‐Alkylidene Oxindoles to Nitroolefins
Author(s) -
Curti Claudio,
Rassu Gloria,
Zambrano Vincenzo,
Pinna Luigi,
Pelosi Giorgio,
Sartori Andrea,
Battistini Lucia,
Zanardi Franca,
Casiraghi Giovanni
Publication year - 2012
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.201202027
Subject(s) - cinchona , bifunctional , enantioselective synthesis , umpolung , organocatalysis , michael reaction , chemistry , thiourea , cinchona alkaloids , reactivity (psychology) , organic chemistry , catalysis , medicine , alternative medicine , pathology , nucleophile
Vinylogy : Advances in asymmetric catalysis using the bifunctional cinchona alkaloid/thioureas enabled an umpolung of the classical C β reactivity of 3‐alkylidene oxindoles, thus allowing the development of the first and sole example of a direct, organocatalytic asymmetric vinylogous Michael (AVM) reaction with nitroolefins.