Brønsted Base Catalyzed One-Pot Synthesis od Stereodefined Six-Member Carbocycles Featuring Transient Trienolates and a Key Intramolecular 1,6-Addition
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Date
2019-07-31Author
Olaizola Aizpuru, Olatz
Iriarte Arrieta, Igor
Zanella, Giovanna
Gómez Bengoa, Enrique
Gamboa Landa, José Ignacio
Oyarbide Garmendia, Juan Miguel
Palomo Nicolau, Claudio
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Angewandte Chemie International Edition 58(40) : 14250-14254 (2019)
Abstract
Acatalyst-driven one-pot reaction sequence is
developed for the enantio- and diastereoselective synthesis of
tetrasubstituted cyclohexenes from simple unsaturated ketones
or thioesters.The method involves atertiary amine/squara-
mide-catalyzed a-selective addition of transiently generated
trienolates to nitroolefins,subsequent base-catalyzed double
bond isomerization, and an intramolecular (vinylogous) 1,6-
addition reaction, arare key carbocyclization step that
proceeded with essentially perfect stereocontrol