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通过环醚化和克莱森重排合成八元环胺的策略。

A Synthetic Strategy toward Eight-Membered Cyclic Amines by Cycloetherification and Claisen Rearrangement.

机构信息

The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 East California Boulevard, MC 101-20, Pasadena, California 91125, United States.

Chemical Kinomics Research Center, KIST and Division of Bio-Medical Science & Technology, KIST-School UST, 5, Hwarangro 14-gil, Seongbuk-gu, Seoul, 02792, Republic of Korea.

出版信息

Org Lett. 2021 May 7;23(9):3300-3303. doi: 10.1021/acs.orglett.1c00763. Epub 2021 Apr 12.

DOI:10.1021/acs.orglett.1c00763
PMID:33844548
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8846577/
Abstract

Eight-membered nitrogen-containing heterocycles were straightforwardly produced by a nickel-catalyzed cycloetherification and subsequent Claisen rearrangement of secondary and tertiary alcohols. In particular, a one-pot transformation was achieved with tertiary alcohols in moderate to good yields. This operationally simple reaction is tolerant of many functional groups and applicable to the synthesis of various medium-sized ring nitrogen-containing heterocycles.

摘要

八元氮杂环化合物可由镍催化的环醚化反应和随后的仲醇和叔醇的克莱森重排反应直接合成。特别是，叔醇可通过一锅法转化以中等至良好的收率得到目标产物。该反应操作简单，对许多官能团具有容忍性，适用于各种中氮杂环的合成。

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本文引用的文献

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Stereoselective synthesis of medium lactams enabled by metal-free hydroalkoxylation/stereospecific [1,3]-rearrangement.非均相催化氢烷氧基化/立体专一性[1,3]-重排反应实现中立体选择性环内酰胺的合成
Nat Commun. 2019 Jul 19;10(1):3234. doi: 10.1038/s41467-019-11245-2.
2
Nickel-Catalyzed Intramolecular C-O Bond Formation: Synthesis of Cyclic Enol Ethers.镍催化的分子内 C-O 键形成：环状烯醇醚的合成。
Angew Chem Int Ed Engl. 2016 Jun 20;55(26):7437-40. doi: 10.1002/anie.201601991. Epub 2016 May 9.
3
Combined rhodium-catalyzed carbon-hydrogen activation and beta-carbon elimination to access eight-membered rings.铑催化的碳氢活化与β-碳消除反应相结合以构建八元环。
Angew Chem Int Ed Engl. 2010;49(3):620-3. doi: 10.1002/anie.200904527.