膦/钯催化合成亚烷基邻苯二甲酸酐、3-脱氧异阿朴啡酸、异阿朴啡酸和异阿朴啡醇。
Phosphine/palladium-catalyzed syntheses of alkylidene phthalans, 3-deoxyisoochracinic acid, isoochracinic acid, and isoochracinol.
机构信息
Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, USA.
出版信息
Org Lett. 2012 Jul 6;14(13):3264-7. doi: 10.1021/ol301154f. Epub 2012 Jun 21.
Abstract
In this study we used sequential catalysis-PPh(3)--catalyzed nucleophilic addition followed by Pd(0)-catalyzed Heck cyclization--to construct complex functionalized alkylidene phthalans rapidly, in high yields, and with good stereoselectivities (E/Z ratios of up to 1:22). The scope of this Michael-Heck reaction includes substrates bearing various substituents around the alkylidene phthalan backbone. Applying this efficient sequential catalysis, we accomplished concise total syntheses of 3-deoxyisoochacinic acid, isoochracinic acid, and isoochracinol.
摘要
在这项研究中，我们使用顺序催化——膦（III）催化的亲核加成，随后是 Pd(0)催化的 Heck 环化——快速构建复杂官能化亚烷基邻苯二甲酰亚胺，产率高，立体选择性好（E/Z 比高达 1:22）。这种迈克尔-赫克反应的范围包括带有各种取代基的亚烷基邻苯二甲酰亚胺骨架的底物。应用这种高效的顺序催化，我们完成了 3-去氧异ochacinic 酸、异ochracinic 酸和异ochracinol 的简洁全合成。
相似文献
1
Phosphine/palladium-catalyzed syntheses of alkylidene phthalans, 3-deoxyisoochracinic acid, isoochracinic acid, and isoochracinol.膦/钯催化合成亚烷基邻苯二甲酸酐、3-脱氧异阿朴啡酸、异阿朴啡酸和异阿朴啡醇。
Org Lett. 2012 Jul 6;14(13):3264-7. doi: 10.1021/ol301154f. Epub 2012 Jun 21.
2
Synthesis of Functionalized Alkylidene Indanes and Indanones through Tandem Phosphine-Palladium Catalysis.通过膦-钯协同催化合成官能化亚烷基茚满和茚满酮。
Org Lett. 2015 May 1;17(9):2058-61. doi: 10.1021/acs.orglett.5b00554. Epub 2015 Apr 14.
3
A Novel synthesis of 2-functionalized benzofurans by palladium-catalyzed cycloisomerization of 2-(1-hydroxyprop-2-ynyl)phenols followed by acid-catalyzed allylic isomerization or allylic nucleophilic substitution.通过钯催化2-(1-羟基丙-2-炔基)苯酚的环异构化，随后进行酸催化的烯丙基异构化或烯丙基亲核取代反应，实现2-官能化苯并呋喃的新型合成。
J Org Chem. 2008 Sep 19;73(18):7336-41. doi: 10.1021/jo801444n. Epub 2008 Aug 26.
4
Allenylphosphonates/allenylphosphine oxides as intermediates/precursors for intramolecular cyclization leading to phosphorus-based indenes, indenones, benzofurans, and isochromenes.烯丙基膦酸酯/烯丙基膦氧化物作为中间体/前体用于分子内环化，生成磷基茚、茚酮、苯并呋喃和异色烯。
J Org Chem. 2012 Jun 15;77(12):5345-56. doi: 10.1021/jo300705f. Epub 2012 Jun 6.
5
Synthesis of each enantiomer of rocaglamide by means of a palladium(0)-catalyzed Nazarov-type cyclization.通过钯（0）催化的 Nazarov 型环化反应合成罗卡酰胺的每个对映异构体。
Angew Chem Int Ed Engl. 2015 May 11;54(20):6037-40. doi: 10.1002/anie.201501374. Epub 2015 Mar 30.
6
Synthesis of functionalized dioxa-aza[7]helicenes using palladium catalyzed arylations.使用钯催化的芳基化反应合成功能化的二氧杂氮杂[7]轮烯。
Org Lett. 2012 Mar 16;14(6):1500-3. doi: 10.1021/ol300236t. Epub 2012 Feb 24.
7
Synthesis of substituted tetrahydrocyclobuta[b]benzofurans by palladium-catalyzed substitution/[2+2] cycloaddition of propargylic carbonates with 2-vinylphenols.钯催化丙炔碳酸酯与 2-乙烯基苯酚的取代/[2+2]环加成合成取代的四氢环丁并[b]苯并呋喃。
Angew Chem Int Ed Engl. 2013 Dec 16;52(51):13597-600. doi: 10.1002/anie.201306903. Epub 2013 Oct 31.
8
Palladium-catalyzed cascade aryl addition/intramolecular lactonization of phthalaldehyde to access 3-aryl- and alkenylphthalides.钯催化的邻苯二甲醛的级联芳基加成/分子内酯化反应，可得到 3-芳基和烯基邻苯二甲酸酐。
J Org Chem. 2010 Sep 3;75(17):6043-5. doi: 10.1021/jo101203b.
9
Construction of 2-substituted-3-functionalized benzofurans via intramolecular Heck coupling: application to enantioselective total synthesis of daphnodorin B.通过分子内 Heck 偶联构建 2-取代-3-官能化苯并呋喃：在手性全合成 daphnodorin B 中的应用。
Org Lett. 2013 Sep 20;15(18):4742-5. doi: 10.1021/ol4021095. Epub 2013 Sep 5.
10
Unified Approach to Furan Natural Products via Phosphine-Palladium Catalysis.通过膦钯催化实现呋喃天然产物的统一方法。
Angew Chem Int Ed Engl. 2021 Apr 12;60(16):8874-8881. doi: 10.1002/anie.202015232. Epub 2021 Mar 8.
引用本文的文献
1
Phosphine-Catalyzed (4+1) Annulation: Rearrangement of Allenylic Carbamates to 3-Pyrrolines through Phosphonium Diene Intermediates.膦催化的(4+1)环化反应：通过鏻二烯中间体将烯丙基氨基甲酸酯重排为3-吡咯啉。
ChemCatChem. 2020 Sep 4;12(17):4352-4372. doi: 10.1002/cctc.202000626. Epub 2020 May 22.
2
Alkynoates as Versatile and Powerful Chemical Tools for the Rapid Assembly of Diverse Heterocycles under Transition-Metal Catalysis: Recent Developments and Challenges.炔酸酯作为在过渡金属催化下快速构建多样杂环的多功能、强效化学工具：最新进展与挑战。
Top Curr Chem (Cham). 2021 Jan 5;379(1):3. doi: 10.1007/s41061-020-00316-4.
3
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.
4
Synthesis of Functionalized Alkylidene Indanes and Indanones through Tandem Phosphine-Palladium Catalysis.通过膦-钯协同催化合成官能化亚烷基茚满和茚满酮。
Org Lett. 2015 May 1;17(9):2058-61. doi: 10.1021/acs.orglett.5b00554. Epub 2015 Apr 14.
5
asymmetric synthesis of the mezzettiaside family of natural products via the iterative use of a dual B-/Pd-catalyzed glycosylation.通过双硼/钯催化糖基化的迭代使用实现梅泽蒂苷类天然产物的不对称合成。
Chem Sci. 2014 Jun;5(6):2230-2234. doi: 10.1039/C4SC00593G.
6
Advances in nucleophilic phosphine catalysis of alkenes, allenes, alkynes, and MBHADs.亲核膦催化烯烃、丙二烯、炔烃和 MBHADs 的进展。
Chem Commun (Camb). 2013 Dec 25;49(99):11588-619. doi: 10.1039/c3cc47368f.
本文引用的文献
1
Development of asymmetric phosphine-promoted annulations of allenes with electron-deficient olefins and imines.不对称膦促进的丙二烯与缺电子烯烃和亚胺的环加成反应的发展。
Chem Commun (Camb). 2012 Feb 7;48(12):1724-32. doi: 10.1039/c1cc15793k. Epub 2011 Nov 10.
2
Diversity-oriented synthesis based on the DPPP-catalyzed mixed double-Michael reactions of electron-deficient acetylenes and β-amino alcohols.基于 DPPP 催化的缺电子炔烃和β-氨基醇的混合双迈克尔反应的导向多样性合成。
Molecules. 2011 May 5;16(5):3802-25. doi: 10.3390/molecules16053802.
3
Allenes as three-carbon units in catalytic cycloadditions: new opportunities with transition-metal catalysts.三碳烯作为催化环加成反应中的单元：过渡金属催化剂的新机遇。
Chemistry. 2011 Jan 10;17(2):418-28. doi: 10.1002/chem.201002366. Epub 2010 Dec 16.
4
Multifunctional chiral phosphine organocatalysts in catalytic asymmetric Morita-Baylis-Hillman and related reactions.多功能手性膦有机催化剂在催化不对称 Morita-Baylis-Hillman 反应及相关反应中的应用。
Acc Chem Res. 2010 Jul 20;43(7):1005-18. doi: 10.1021/ar900271g.
5
Diphosphine-catalyzed mixed double-Michael reaction: a unified synthesis of indolines, dihydropyrrolopyridines, benzimidazolines, tetrahydroquinolines, tetrahydroisoquinolines, dihydrobenzo-1,4-oxazines, and dihydrobenzo-3,1-oxazines.二膦催化的混合双迈克尔反应：吲哚啉、二氢吡啶并吡啶、苯并咪唑啉、四氢喹啉、四氢异喹啉、二氢苯并-1,4-恶嗪和二氢苯并-3,1-恶嗪的统一合成。
Org Lett. 2010 Mar 5;12(5):1084-7. doi: 10.1021/ol100078w.
6
A simple and mild synthesis of 1H-isochromenes and (Z)-1-alkylidene-1,3-dihydroisobenzofurans by the iodocyclization of 2-(1-alkynyl)benzylic alcohols.2-(1-炔基)苄基醇的碘环化反应合成 1H-异色烯和(Z)-1-亚烷基-1,3-二氢异苯并呋喃
J Org Chem. 2010 Feb 5;75(3):897-901. doi: 10.1021/jo902333y.
7
Enantioselective catalysis and complexity generation from allenoates.手性催化与丙二烯酸酯的复杂度生成。
Chem Soc Rev. 2009 Nov;38(11):3102-16. doi: 10.1039/b816700c. Epub 2009 Jul 24.
8
Mitsunobu and related reactions: advances and applications.光延反应及相关反应：进展与应用
Chem Rev. 2009 Jun;109(6):2551-651. doi: 10.1021/cr800278z.
9
Synthesis of (E)-3-(isobenzofuran-3(1H)-ylidene)indolin-2-ones by the palladium-catalyzed intramolecular C-H functionalization process.通过钯催化的分子内C-H官能化过程合成（E）-3-（异苯并呋喃-3（1H）-亚基）吲哚啉-2-酮
J Org Chem. 2009 May 1;74(9):3569-72. doi: 10.1021/jo900437p.
10
Phosphine-triggered synthesis of functionalized cyclic compounds.磷化氢引发的功能化环状化合物的合成。
Chem Soc Rev. 2008 Jun;37(6):1140-52. doi: 10.1039/b717758e. Epub 2008 Mar 26.
Zotero 插件