Synthesis of 1,4‐Cyclohexadiene Carboxylates through a Formal [2+4]‐Cycloaddition of Propiolates under Cobalt Catalysis,Helvetica Chimica Acta

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Synthesis of 1,4‐Cyclohexadiene Carboxylates through a Formal [2+4]‐Cycloaddition of Propiolates under Cobalt Catalysis
Helvetica Chimica Acta ( IF 1.5 ) Pub Date : 2020-10-13 , DOI: 10.1002/hlca.202000175
Julie Charpentier ₁ , Francis Voirol ₁ , Felix Flachsmann ₁ , Silvia Tanner ₁ , Natalie Aeberli ₁ , Gerhard Brunner ₁ , Andreas Goeke ₁

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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 β‐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.

中文翻译：

在钴催化下通过丙酸酯的[2 + 4]-环加成反应合成1,4-环己二烯羧酸酯

由锌还原CoBr ₂（dppe）形成的低价钴（I）络合物，可作为催化剂将β-烷基，环烷基和芳基取代的丙酸酯有效[2 + 4]环加成二烯。此转化可产生合成相关的1,4-环己二烯羧酸盐，收率好至极好。此外，目标化合物是新颖的先导结构，可用于发现来自果味，花香和辛辣气味家族的香料成分。

更新日期：2020-12-11

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