ABSTRACT
The γ-lactam ring is a prominent feature in medicinal chemistry, and its synthesis has garnered significant interest due to its valuable properties. Among the γ-lactams, 2-oxopyrrolidine-3-carbonitrile derivatives stand out as versatile synthons that can be readily transformed into a variety of other functional groups. In this work, we successfully synthesized highly functionalized 3-cyano-2-pyrrolidinones with moderate to good overall yields using the Ugi reaction followed by intramolecular Michael addition. The process demonstrated excellent diastereoselectivity and showed good tolerance to a range of isonitriles and carbonyl compounds.
ABSTRACT
BINOL derivatives have shown relevant biological activities and are important chiral ligands and catalysts. Due to these properties, their asymmetric synthesis has attracted the interest of the scientific community. In this work, we present an overview of the most efficient methods to obtain chiral BINOLs, highlighting the use of metal complexes and organocatalysts as well as kinetic resolution. Further derivatizations of BINOLs are also discussed.
Subject(s)
Naphthols , Stereoisomerism , Catalysis , LigandsABSTRACT
Multicomponent reactions (MCRs) undoubtedly correspond to one of the synthetic strategies that best fit the new demands of chemistry for presenting high atom economy and enabling molecular diversity. However, many challenges still exist when products possessing stereogenic centres are formed. The field of asymmetric catalytic reactions has achieved significant progress in recent decades; new applications for chiral ligands and catalysts have been demonstrated and new catalysts have been specifically designed for challenging chemical conversions. In this sense, highly efficient approaches for classic multicomponent reactions such as the Ugi reaction and a number of new asymmetric MCRs have been described. In this review we discuss the recent developments that enable catalytic enantioselective MCRs including the proposed mechanistic pathways.