Stereo-controlled synthesis of polyheterocycles via diene-transmissive hetero-Diels-Alder reaction of β,γ-unsaturated α-keto esters
Stereo-controlled synthesis of polyheterocycles via diene-transmissive hetero-Diels-Alder reaction of β,γ-unsaturated α-keto esters
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通过β,γ-不饱和α-酮酯的二烯传输杂Diels-Alder反应立体控制合成多杂环
DOI：
10.1039/c5ob00503e
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发表时间：
2015
影响因子：
3.2
通讯作者：
Taiichiro Miyazawaa and Takao Saito*
中科院分区：
文献类型：
--
作者：
Takashi Otani,* Yumiko Tamai;Kazunori Seki;Tomohiro Kikuchi;Taiichiro Miyazawaa and Takao Saito*
本文描述了以β，γ-不饱和α-酮酯为原料，基于二烯透射的杂diels - alder反应立体选择性合成多环融合杂环化合物。该方案包括与富电子亲二烯试剂的初始内或外选择性diols - alder （DA）反应，酯羰基与Tebbe试剂的甲基化反应，以及与缺电子亲二烯试剂的立体选择性第二DA反应。在初始反应中使用对映选择性DA反应可以获得具有多个手性中心的手性多环融合杂环化合物。
We describe the stereoselective synthesis of polyring-fused heterocyclic compounds based on diene-transmissive hetero-Diels–Alder reactions utilizing β,γ-unsaturated α-keto esters. This protocol involves the initial endo- or exo-selective Diels–Alder (DA) reactions with electron-rich dienophiles, methylenation of the ester carbonyl groups with the Tebbe reagent, and a stereoselective second DA reaction with electron-deficient dienophiles. The use of enantioselective DA reactions in the initial reaction enables access to chiral polyring-fused heterocyclic compounds with multiple chiral centres.