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有机膦催化的[4C+X]环化反应。

Organophosphine-Catalyzed [4C+X] Annulations.

机构信息

College of Chemistry and Bioengineering, Hunan University of Science and Engineering, Yongzhou 425199, Hunan, China.

Institute for Advanced Studies, Wuhan University, 299 Bayi Road, Wuchang District, Wuhan 430072, Hubei, China.

出版信息

Molecules. 2018 Nov 19;23(11):3022. doi: 10.3390/molecules23113022.

DOI:10.3390/molecules23113022
PMID:30463230
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6278662/
Abstract

In recent years, there have been extraordinary developments of organophosphine-catalyzed reactions. This includes progress in the area of [4C+X] annulations, which are of particular interest due to their potential for the rapid construction of 5⁻8-membered cyclic products. In this short overview, we summarize the remarkable progress, emphasizing reaction mechanisms and key intermediates involved in the processes. The discussion is classified according to the type of electrophilic reactants that acted as ₄ synthons in the annulation process, in the order of α-alkyl allenoates, γ-alkyl allenoates, α-methyl allene ketones, β'-OAc allenoate, δ-OAc allenoate, activated dienes and cyclobutenones.

摘要

近年来,有机膦催化反应取得了非凡的发展。这包括[4C+X]环化反应领域的进展,由于其快速构建 5⁻8 元环产物的潜力,这些反应引起了特别关注。在这个简短的综述中,我们总结了显著的进展,强调了反应机制和过程中涉及的关键中间体。讨论根据在环化过程中作为 4 元合成子的亲电反应物的类型进行分类,顺序为α-烷基丙二烯酸酯、γ-烷基丙二烯酸酯、α-甲基丙二烯酮、β'-OAc 丙二烯酸酯、δ-OAc 丙二烯酸酯、活化二烯和环丁烯酮。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4f24/6278662/e1d789cdaf5e/molecules-23-03022-sch017.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4f24/6278662/9e1ae7fdd53a/molecules-23-03022-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4f24/6278662/a45ca2e982e4/molecules-23-03022-sch006.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4f24/6278662/60f50d83edaf/molecules-23-03022-sch008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4f24/6278662/6fc08f26d056/molecules-23-03022-sch009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4f24/6278662/098e175bedd3/molecules-23-03022-sch011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4f24/6278662/43b9a89d05d1/molecules-23-03022-sch012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4f24/6278662/df024866764f/molecules-23-03022-sch013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4f24/6278662/e4c16d3c913f/molecules-23-03022-sch014.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4f24/6278662/dc33e5435360/molecules-23-03022-sch015.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4f24/6278662/e1d789cdaf5e/molecules-23-03022-sch017.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4f24/6278662/978542f00574/molecules-23-03022-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4f24/6278662/4227751bf1fa/molecules-23-03022-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4f24/6278662/002da538393a/molecules-23-03022-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4f24/6278662/9e1ae7fdd53a/molecules-23-03022-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4f24/6278662/a45ca2e982e4/molecules-23-03022-sch006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4f24/6278662/da7858cea14e/molecules-23-03022-sch007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4f24/6278662/60f50d83edaf/molecules-23-03022-sch008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4f24/6278662/6fc08f26d056/molecules-23-03022-sch009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4f24/6278662/098e175bedd3/molecules-23-03022-sch011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4f24/6278662/43b9a89d05d1/molecules-23-03022-sch012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4f24/6278662/df024866764f/molecules-23-03022-sch013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4f24/6278662/e4c16d3c913f/molecules-23-03022-sch014.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4f24/6278662/dc33e5435360/molecules-23-03022-sch015.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4f24/6278662/e1d789cdaf5e/molecules-23-03022-sch017.jpg

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本文引用的文献

1
Phosphine Organocatalysis.膦有机催化。
Chem Rev. 2018 Oct 24;118(20):10049-10293. doi: 10.1021/acs.chemrev.8b00081. Epub 2018 Sep 27.
2
Catalytic Enantioselective Synthesis of Guvacine Derivatives through [4 + 2] Annulations of Imines with α-Methylallenoates.通过亚甲基丙二酸盐与亚胺的[4 + 2]环加成反应催化对映选择性合成葫芦巴碱衍生物。
Org Lett. 2018 Oct 5;20(19):6089-6093. doi: 10.1021/acs.orglett.8b02489. Epub 2018 Sep 24.
3
Phosphine-Catalyzed Asymmetric Organic Reactions.膦催化的不对称有机反应。
Chem Rev. 2018 Sep 26;118(18):9344-9411. doi: 10.1021/acs.chemrev.8b00261. Epub 2018 Sep 11.
4
Phosphine-Catalyzed Enantioselective [4 + 2] Cycloaddition-Semipinacol-Type-Rearrangement Reaction of Morita-Baylis-Hillman Carbonates.膦催化的 Morita-Baylis-Hillman 碳酸酯的对映选择性[4+2]环加成-半频哪醇型重排反应。
Org Lett. 2018 Jul 20;20(14):4250-4254. doi: 10.1021/acs.orglett.8b01661. Epub 2018 Jun 28.
5
Construction of Complex 1,3-Cyclohexadienes via Phosphine-Catalyzed (4 + 2) Annulations of δ-Acetoxy Allenoates and Ketones.通过膦催化 δ-乙酰氧基丙炔酸酯和酮的(4 + 2)环加成反应构建稠合 1,3-环己二烯
Org Lett. 2017 Oct 6;19(19):5462-5465. doi: 10.1021/acs.orglett.7b02787. Epub 2017 Sep 27.
6
Enantioselective Phosphine-Catalyzed Formal [4+4] Annulation of α,β-Unsaturated Imines and Allene Ketones: Construction of Eight-Membered Rings.手性膦催化的α,β-不饱和亚胺和烯酮的[4+4]环加成反应:八元环的构建。
Angew Chem Int Ed Engl. 2017 Nov 6;56(45):14222-14226. doi: 10.1002/anie.201707183. Epub 2017 Oct 10.
7
Nucleophilic Chiral Phosphines: Powerful and Versatile Catalysts for Asymmetric Annulations.亲核手性膦:用于不对称环化反应的强大且通用的催化剂。
Aldrichimica Acta. 2016;49(1):3-13.
8
Phosphine-Catalyzed Enantioselective [4 + 3] Annulation of Allenoates with C,N-Cyclic Azomethine Imines: Synthesis of Quinazoline-Based Tricyclic Heterocycles.膦催化的丙二烯酸酯与 C,N-环亚甲胺的对映选择性[4 + 3]环化反应:基于喹唑啉的三环杂环的合成。
Org Lett. 2016 Nov 4;18(21):5644-5647. doi: 10.1021/acs.orglett.6b02885. Epub 2016 Oct 21.
9
Cyclopenta[b]annulation of Heteroarenes by Organocatalytic γ'[C(sp )-H] Functionalization of Ynones.通过有机催化的炔酮γ'[C(sp )-H]官能团化实现杂芳烃的环戊并[b]环化反应
Chemistry. 2016 Dec 19;22(51):18316-18321. doi: 10.1002/chem.201604562. Epub 2016 Oct 31.
10
Amino Acid-Derived Bifunctional Phosphines for Enantioselective Transformations.氨基酸衍生双功能膦配体用于对映选择性转化。
Acc Chem Res. 2016 Jul 19;49(7):1369-78. doi: 10.1021/acs.accounts.6b00163. Epub 2016 Jun 16.