Bronsted Acid-Initiated Formal [1,3]-Rearrangement Dictated by β‐Substituted Ene-Aldimines
Bronsted Acid-Initiated Formal [1,3]-Rearrangement Dictated by β‐Substituted Ene-Aldimines
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β-取代烯醛亚胺引发的布朗斯台德酸引发的正式 [1,3]-重排
DOI：
10.1021/acs.orglett.9b01533
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发表时间：
2019
期刊：
影响因子：
5.2
通讯作者：
and Norie Momiyama
中科院分区：
文献类型：
--
作者：
Chanantida Jongwohan;Yasushi Honda;Toshiyasu Suzuki;Takeshi Fujinami;Kiyohiro Adachi;and Norie Momiyama
烯醛胺的重排是产生同构胺的有用反应。尽管它们在合成化学中很有用，但在2位取代的均烯丙胺的重排仍然是难以捉摸的。在本研究中，Brønsted酸引发的烯醛胺的形式[1,3]重排被开发出来，以合成2,4,4取代的同烯丙基胺，而这些胺在以前是无法获得的。我们的研究揭示了一种分子间途径，其中重排通过质子介导的2-偶氮离子进行。
The rearrangement of ene-aldimines is a useful reaction for affording homoallylic amines. Despite their utilities in synthetic chemistry, the rearrangement for accessing homoallylic amines substituted at the 2-position remains elusive. In this study, the Brønsted acid-initiated formal [1,3]-rearrangement of ene-aldimines was developed to synthesize 2,4,4-substituted homoallylic amines that were otherwise inaccessible previously. Our study reveals an intermolecular pathway in which the rearrangement proceeds via a protonation-mediated 2-azaallenium cation.