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Synthesis of Seven-Membered Cross-Conjugated Cyclic Trienes by 8π Electrocyclic Reaction
Organic Letters ( IF 4.9 ) Pub Date : 2021-10-29 , DOI: 10.1021/acs.orglett.1c03383 Ranmaru Kato 1 , Hiroki Saito 1 , Shoko Uda 1 , Daisuke Domon 1 , Kazutada Ikeuchi 2 , Takahiro Suzuki 2 , Keiji Tanino 2
Organic Letters ( IF 4.9 ) Pub Date : 2021-10-29 , DOI: 10.1021/acs.orglett.1c03383 Ranmaru Kato 1 , Hiroki Saito 1 , Shoko Uda 1 , Daisuke Domon 1 , Kazutada Ikeuchi 2 , Takahiro Suzuki 2 , Keiji Tanino 2
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A method for the synthesis of 3-methylene-1,4-cycloheptadiene derivatives via an 8π electrocyclization reaction was developed. The triene substrate bearing a phosphate or carbamate group was prepared from γ,δ-unsaturated esters and α,β-unsaturated aldehydes in four steps. Upon treatment with NaHMDS or KHMDS, the substrate formed a heptatrienyl anion, which underwent electrocyclization and subsequent β-elimination of the leaving group. The product could be converted into a tropylium salt in two steps.
中文翻译：
8π电环反应合成七元交叉共轭环状三烯
开发了一种通过8π电环化反应合成3-亚甲基-1,4-环庚二烯衍生物的方法。由γ,δ-不饱和酯和α,β-不饱和醛分四步制备带有磷酸或氨基甲酸酯基团的三烯底物。在用 NaHMDS 或 KHMDS 处理后，底物形成了一个庚三烯基阴离子，它经历了电环化和随后的离去基团的 β-消除。该产物可以分两步转化为鎓盐。
更新日期：2021-11-19
中文翻译：
8π电环反应合成七元交叉共轭环状三烯
开发了一种通过8π电环化反应合成3-亚甲基-1,4-环庚二烯衍生物的方法。由γ,δ-不饱和酯和α,β-不饱和醛分四步制备带有磷酸或氨基甲酸酯基团的三烯底物。在用 NaHMDS 或 KHMDS 处理后，底物形成了一个庚三烯基阴离子，它经历了电环化和随后的离去基团的 β-消除。该产物可以分两步转化为鎓盐。
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