4.3 Article

Synthesis of 1,4-Cyclohexadiene Carboxylates through a Formal [2+4]-Cycloaddition of Propiolates under Cobalt Catalysis

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HELVETICA CHIMICA ACTA
卷 103, 期 12, 页码 -

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WILEY-V C H VERLAG GMBH
DOI: 10.1002/hlca.202000175

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alkynes; catalysis; cobalt; cycloaddition; cyclohexadiene; fragrance chemistry

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A low-valent cobalt(I) complex, formed from the reduction of CoBr2(dppe) with zinc, acts as catalyst for the efficient [2+4] cycloaddition of beta-alkyl, cycloalkyl and aryl substituted propiolates to dienes. This transformation yields synthetically relevant 1,4-cyclohexadiene carboxylates in good to excellent yields. Furthermore, the target compounds are novel lead structures for the discovery of fragrance ingredients from the fruity, floral and spicy odor family.

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