Pd-catalyzed borylative polycyclization of enediynes to allylboronates.
Pd-catalyzed dicyclization of 6-ene-1,11-diynes with bis(pinacolato)diboron affords synthetically useful allylboronates under smooth conditions. Two new C-C and one C-B bonds are stereospecifically formed in a single operation. The stereochemical outcome depends on the starting alkene configuration. The reaction is general and has been applied to differently substituted enediynes. Isolation of intermediate 1,3-dienes suggests a regioselective beta-hydrogen elimination along the reaction pathway.
Marco-Martínez
Juan
J
Departamento de Química Orgánica, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain.
Buñuel
Elena
E
Muñoz-Rodríguez
Rebeca
R
Cárdenas
Diego J
DJ
D001896:Boron Compounds / Q000737:chemistry*; D001897:Boronic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002074:Butanones / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D053281:Enediynes / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
D001896:Boron Compounds; D001897:Boronic Acids; D002074:Butanones; D053281:Enediynes; C463639:bis(pinacolato)diboron; D010165:Palladium