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Rhodium(I)-Catalyzed Bridged [5+2] Cycloaddition of cis-Allene-vinylcyclopropanes to Synthesize the Bicyclo[4.3.1]decane Skeleton.铑（I）催化顺式丙二烯-乙烯基环丙烷的桥接[5+2]环加成反应合成双环[4.3.1]癸烷骨架。
Angew Chem Int Ed Engl. 2017 Jul 17;56(30):8667-8671. doi: 10.1002/anie.201702288. Epub 2017 Jun 23.
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The chemistry of ynol and thioynol ethers.炔醇和硫代炔醇醚的化学性质。
Org Biomol Chem. 2016 Oct 18;14(41):9695-9711. doi: 10.1039/c6ob01776b.
3
Tandem Bond-Forming Reactions of 1-Alkynyl Ethers.1-炔基醚的串联键形成反应。
Acc Chem Res. 2016 Jun 21;49(6):1168-81. doi: 10.1021/acs.accounts.6b00107. Epub 2016 May 19.
4
Computational ligand design in enantio- and diastereoselective ynamide [5+2] cycloisomerization.对映选择性和非对映选择性烯酰胺[5+2]环异构化反应中的计算配体设计
Nat Commun. 2016 Jan 5;7:10109. doi: 10.1038/ncomms10109.
5
Rhodium-Catalyzed Stereoselective Intramolecular [5 + 2] Cycloaddition of 3-Acyloxy 1,4-Enyne and Alkene.铑催化的3-酰氧基-1,4-烯炔与烯烃的立体选择性分子内[5+2]环加成反应
Org Lett. 2015 Oct 16;17(20):5128-31. doi: 10.1021/acs.orglett.5b02665. Epub 2015 Oct 6.
6
Catalytic Efficiency Is a Function of How Rhodium(I) (5 + 2) Catalysts Accommodate a Conserved Substrate Transition State Geometry: Induced Fit Model for Explaining Transition Metal Catalysis.催化效率是铑（I）（5 + 2）催化剂如何适应保守底物过渡态几何结构的函数：解释过渡金属催化的诱导契合模型。
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7
Tetramethyleneethane Equivalents: Recursive Reagents for Serialized Cycloadditions.四亚甲基乙烷等价物：用于序列化环加成反应的递归试剂。
J Am Chem Soc. 2015 Jul 22;137(28):9088-93. doi: 10.1021/jacs.5b04091. Epub 2015 May 29.
8
Function through bio-inspired, synthesis-informed design: step-economical syntheses of designed kinase inhibitors†Dedicated to Max Malacria, a friend and scholar whose science and creative contributions to step-economical synthesis have inspired us all and moved the field closer to the ideal.‡Electronic supplementary information (ESI) available: Synthetic procedures and spectral data. See DOI: 10.1039/c4qo00228hClick here for additional data file.通过仿生、合成导向设计实现功能：设计激酶抑制剂的分步经济合成† 献给马克斯·马拉克里亚，一位朋友和学者，他对分步经济合成的科学及创造性贡献激励了我们所有人，并推动该领域更接近理想状态。‡ 可获取电子补充信息（ESI）：合成步骤和光谱数据。见DOI：10.1039/c4qo00228h 点击此处获取额外数据文件。
Org Chem Front. 2014 Dec 29;1(10):1166-1171. doi: 10.1039/c4qo00228h. Epub 2014 Oct 6.
9
Iridium catalyzed carbocyclizations: efficient (5+2) cycloadditions of vinylcyclopropanes and alkynes.铱催化的碳环化反应：乙烯基环丙烷与炔烃的高效（5+2）环加成反应
Chemistry. 2015 Jan 7;21(2):531-5. doi: 10.1002/chem.201405729. Epub 2014 Nov 20.
10
Reactivity and chemoselectivity of allenes in Rh(I)-catalyzed intermolecular (5 + 2) cycloadditions with vinylcyclopropanes: allene-mediated rhodacycle formation can poison Rh(I)-catalyzed cycloadditions.联烯在铑（I）催化下与乙烯基环丙烷发生分子间（5 + 2）环加成反应的反应活性和化学选择性：联烯介导的铑环形成会使铑（I）催化的环加成反应中毒。
J Am Chem Soc. 2014 Dec 10;136(49):17273-83. doi: 10.1021/ja5098308. Epub 2014 Nov 24.

铑催化的分子间[5+2]环加成反应中 Ynol 醚作为偕二酮等价物。

Ynol Ethers as Ketene Equivalents in Rhodium-Catalyzed Intermolecular [5 + 2] Cycloaddition Reactions.

机构信息

Departments of Chemistry and Chemical and Systems Biology, Stanford University , Stanford, California 94305, United States.

出版信息

Org Lett. 2017 Nov 3;19(21):5810-5813. doi: 10.1021/acs.orglett.7b02765.

DOI:10.1021/acs.orglett.7b02765
PMID:29034684
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5833981/
Abstract

The previously unexplored metal-catalyzed [5 + 2] cycloadditions of vinylcyclopropanes (VCPs) and electron-rich alkynes (ynol ethers) have been found to provide a highly efficient, direct route to dioxygenated seven-membered rings, a common feature of numerous natural and non-natural targets and building blocks for synthesis. The reactions proceed in high yield at room temperature and tolerate a broad range of functionalities. Substituted VCPs were found to react with high regioselectivity.

摘要

先前未被探索的金属催化[5+2]环加成反应，即乙烯基环丙烷（VCPs）和富电子炔烃（ynol 醚）的反应，已被发现为提供高效、直接的途径，合成含有氧原子的七元环，这是许多天然和非天然目标以及合成砌块的共同特征。反应在室温下以高产率进行，并能容忍广泛的官能团。取代的 VCPs 被发现具有高区域选择性反应。