Bronsted Acid Catalyzed Multicomponent Synthesis of Phosphorus and Fluorine-Derived γ-Lactam Derivatives

A Brönsted acid multicomponent reaction between pyruvate derivatives, amines, and aldehydes for the preparation of phosphorus and fluorine substituted γ-lactam derivatives is presented. Depending on the substitution in the resulting 1,5-dihydro-2H-pyrrol-2-one substrates, the reaction provides enol...

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Bibliographic Details
Authors: Del Corte Solaguren-Beascoa, Xabier, López Francés, Adrián, Maestro Burzaco, Aitor, Martínez de Marigorta Izaga, Edorta, Palacios Gambra, Francisco Javier, Vicario Hernando, Javier
Format: article
Publication Date:2020
Country:España
Institution:Universidad del País Vasco
Repository:Addi. Archivo Digital para la Docencia y la Investigación
OAI Identifier:oai:addi.ehu.eus:10810/70058
Online Access:http://hdl.handle.net/10810/70058
Access Level:Open access
Keyword:gamma-lactams
multicomponent reactions
asymmetric organocatalysis
chiral phosphoric acids
Description
Summary:A Brönsted acid multicomponent reaction between pyruvate derivatives, amines, and aldehydes for the preparation of phosphorus and fluorine substituted γ-lactam derivatives is presented. Depending on the substitution in the resulting 1,5-dihydro-2H-pyrrol-2-one substrates, the reaction provides enol- or enamine-derived γ-lactams. Some enantioselective examples of this reaction are also reported using chiral phosphoric acids as organocatalysts. Moreover, several synthetic applications of γ-lactam derivatives are presented including some examples of highly diastereoselective transformations