Efficient synthesis of tetrasubstituted alkenes by allylsilane-terminated domino-Heck double cyclisation |
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Authors: | Tietze Lutz F Kahle Klaus Raschke Thomas |
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Affiliation: | Institut für Organische Chemie der Georg-August-Universit?t G?ttingen, Germany. ltietze@gwdg.de |
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Abstract: | The domino-Heck double cyclisation of the arylbromides 1, which contain an allylsilane and an alkyne moiety and are easily accessible by an addition of the corresponding lithiated alkynes 5 to the aldehydes 4, leads to the tetrasubstituted alkenes 2 and 3 in good yield. The reaction produces exclusively compounds with an E double bond and additionally proceeds with good to excellent induced diastereoselectivity in the case of 1e and 1f. Irradiation of 2e leads to a steady state equilibrium of the E and Z compounds in a 1:1 ratio. |
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