Organocatalytic cascade reactions: diversity-oriented synthesis for the construction of hydroisoquinoline scaffolds.
The organocatalytic enantioselective synthesis of highly functionalized hydroisoquinolines by trienamine-mediated [4+2]-cycloaddition/nucleophilic ring-closing reaction cascade sequence of cyanoacrylamides with 2,4-dienals is presented. The corresponding cycloadducts are formed in high yields and excellent stereoselectivities. Moreover, a series of transformations demonstrate the synthetic application of the obtained hydroisoquinolines.
Center for Catalysis, Department of Chemistry, Aarhus University, 8000 Aarhus C, Denmark. kaj@chem.au.dk.
Clarisa Villegas
CV
Gómez
David Cruz
DC
Cruz
Rasmus
R
Mose
Karl Anker
KA
Jørgensen
D000178:Acrylamides / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D061565:Cycloaddition Reaction / Q000379:methods*; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D000178:Acrylamides; D000447:Aldehydes; D007546:Isoquinolines