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Pd-Catalyzed Borylative Polycyclization of Enediynes to Allylboronates

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journal contribution
posted on 21.08.2008 by Juan Marco-Martínez, Elena Buñuel, Rebeca Muñoz-Rodríguez, Diego J. Cárdenas
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 β-hydrogen elimination along the reaction pathway.