An environmentally benign synthesis of cis-2,6-disubstituted tetrahydropyrans via indium-mediated tandem allylation/Prins cyclization reaction.
An environmentally benign synthesis of cis-2,6-disubstituted tetrahydropyrans via indium-mediated tandem allylation/Prins cyclization reaction.
复制标题
通过铟介导的串联烯丙基化/Prins环化反应环境友好地合成顺式2,6-二取代四氢吡喃。
DOI：
10.1021/jo7016857
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发表时间：
2008
期刊：
影响因子：
--
通讯作者：
Minehan,ThomasG
中科院分区：
文献类型：
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作者：
Pham,Minh;Allatabakhsh,Amir;Minehan,ThomasG
在金属铟存在下，3-碘-2-[（三甲基硅基）甲基]丙烯（1）与依次加入的醛反应，以良好的产率得到顺式-2，6-二取代四氢吡喃。有证据表明，InI，醛（R1 CHO）烯丙基化后形成的水介质中，作为甲硅烷基-普林斯反应的促进剂与第二当量的添加醛（R2 CHO）。通过这种一锅法，三组分偶联过程的环己烯基稠合吡喃的制备，是一个简短的正式合成（±）-centrolobine。
In the presence of indium metal, 3-iodo-2-[(trimethylsilyl)methyl]propene (1) reacts with sequentially added aldehydes to providecis-2,6-disubstituted tetrahydropyrans in good yields. Evidence suggests that InI, formed upon aldehyde (R1CHO) allylation in aqueous media, acts as a promoter for the silyl-Prins reaction with the second equivalent of added aldehyde (R2CHO). The preparation of cyclohexenyl-fused pyrans via this one-pot, three-component coupling process is presented, as is a short formal synthesis of (±)-centrolobine.