Enantioenriched indole derivatives are widely found in natural products, pharmaceuticals and bioactive compounds. Therefore, developing efficient methods for the synthesis of enantioenriched indole derivatives has become an important goal in...
The chiral phosphoric acid catalyzed asymmetric Diels-Alder reactions of 2-vinylindoles with methyleneindolinones have been established, which efficiently construct the spiro[tetrahydrocarbazole-3,3'-oxindole] architecture with one quaternary and three contiguous stereogenic centers in high yields (up to 99%) and excellent stereoselectivities (up to >95:5 dr, 97% ee). This reaction not only provides an efficient strategy to access enantioenriched spiro[tetrahydrocarbazole-3,3'-oxindoles] based on hydrogen-bonding activation mode but also supplies successful examples of catalytic asymmetric Diels-Alder reactions for constructing complex spiro-frameworks with optical purity.
New three-component domino reaction providing divergent approaches to multi-functionalized fused pyrroles with different substituted patterns have been established (40 examples). The direct C(sp3)–N bond formation was achieved through intermolecular allylic amination in a one-pot operation; and N-arylation of amines was realized by varying N-amino acid enaminones. The reaction is easy to perform simply by mixing three common reactants in acetic acid under microwave heating. The reaction proceeds at fast rates and can be finished within 30 min, which makes workup convenient to give good chemical yields.
The title reaction has been established in the presence of chiral phosphoric acid, affording chiral chroman derivatives bearing an indole moiety in high yields and with moderate to good stereoselectivities.
The first catalytic asymmetric construction of the biologically important dibenzoA C H T U N G T R E N N U N G [1,4]diazepine scaffold has been established via SPINOL-derived chiral phosphoric acid-catalyzed three-component reactions of aldehydes, 1,2-phenylenediamines and cyclohexane-1,3-diones, which afforded structurally complex and diverse dibenzoA C H T U N G T R E N N U N G [1,4]diazepines in high yields and good enantioselectivities (up to 98% yield, 92:8 er). This transformation also represents the first catalytic asymmetric version of this threecomponent reaction and provides an easy access to structurally rigid seven-membered chiral heterocycles.
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