Reaction of carbonyl compounds with [(trimethylsilyl) propargyl]dii-sobutyltelluronium bromide mediated by different strong bases: Highly regioselective synthesis of (trimethylsilyl) propargyl alcohol and highly stereoselective synthesis of cis-(trimethylsilyl) alkynyl epoxides
Reaction of carbonyl compounds with [(trimethylsilyl) propargyl]dii-sobutyltelluronium bromide mediated by different strong bases: Highly regioselective synthesis of (trimethylsilyl) propargyl alcohol and highly stereoselective synthesis of cis-(trimethylsilyl) alkynyl epoxides
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不同强碱介导的羰基化合物与[(三甲基硅基)炔丙基]二异丁基碲溴化物的反应：高区域选择性合成(三甲基硅基)炔丙醇和高立体选择性合成顺式(三甲基硅基)炔基环氧化物
DOI：
10.1021/jo00050a042
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发表时间：
1992
影响因子：
3.6
通讯作者：
Jiong
中科院分区：
文献类型：
--
作者：
Zhang‐Lin Zhou;Yaozeng Huang;Li;Jiong
[(三甲基硅基)炔丙基)]二异丁基碲溴化物(1)经烯丙基或芳基锂试剂处理后，通过不稳定的瞬态四有机基碲中间体进行锂-碲交换反应，原位生成的锂物种与羰基化合物反应，以高收率和高区域选择性生成(三甲基硅基)-炔丙醇2。然而，当用非亲核碱（例如LDA或2,2,6,6-四甲基哌啶锂）处理碲盐I时，形成了适度稳定的甲硅烷基化碲叶立德。甲硅烷基化碲叶立德与羰基化合物反应，以良好至优异的产率和高顺式立体选择性提供(三甲基甲硅烷基)炔基环氧化物11
[(Trimethylsilyl)propargyl)]diisobutyltelluronium bromide (1), after being treated with allyl- or aryllithium reagent, undergoes a lithium-tellurium exchange reaction via an unstable transient tetraorganyltellurium intermediate, and the in situ generated lithium species reacts with carbonyl compounds to give (trimethylsilyl)-propargyl alcohols 2 in high yields with high regioselectivity. However, when the telluronium salt I was treated with nonnucleophilic bases such as LDA or lithium 2,2,6,6-tetramethylpiperidide, the moderately stabilized silylated telluronium ylide formed. The silylated telluronium ylide reacted with carbonyl compounds to afford (trimethylsilyl)alkynyl epoxides 11 in good to excellent yields with high cis stereoselectivity