Abstract
Pd-catalyzed bicyclization of 1-ene-6,11-diynes with bis(pinacolato)diboron smoothly affords synthetically useful homoallylic alkylboronates under mild conditions, avoiding the use of highly nucleophilic or basic reagents. One C-B bond and two new C-C bonds are created, and two new stereogenic centers are stereospecifically formed in a single tandem operation. The obtained products suggest a cascade reaction in which the last step is the transmetalation of bis(pinacolato)diboron, this being faster than a possible β-hydride elimination process. The reaction is general and has been applied to enediynes with different substituents on the alkene unit, the bridging groups, and the alkyne moiety. The bicyclized alkylboronates thus obtained can be functionalized by oxidation to alcohols, formation of trifluoroborate salts, or by Suzuki coupling reactions.
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