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Regioselective Cobalt-Catalyzed Alder-ene Reaction toward Silicon- and Boron-Functionalized Building Blocks

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journal contribution
posted on 21.01.2011, 00:00 by Gerhard Hilt, Florian Erver, Klaus Harms
The cobalt-catalyzed formal Alder-ene reaction of functionalized alkenes and alkynes leads to bifunctionalized 1,4-dienes in high yields and excellent regio- and stereoselectivities. The silicon-functionalized building blocks are easily converted into iodo-functionalized derivatives and in combination with boron-functionalized building blocks polyenes can be generated utilizing a Suzuki cross-coupling. In addition, building blocks incorporating allylic silane functionalities can be used in Sakurai allylation or Prins-type cyclization reactions for the synthesis of heterocyclic products such as tetrahydrofuranes or tetrahydropyranes.