通过用π-亲核试剂捕获碳正离子合成β-杂芳基丙酸酯。
Synthesis of β-Heteroaryl Propionates via Trapping of Carbocations with π-Nucleophiles.
作者信息
Fu Tsung-Hao, Bonaparte Amy, Martin Stephen F
机构信息
Department of Chemistry and Biochemistry, The University of Texas, Austin, TX USA 78712.
出版信息
Tetrahedron Lett. 2009 Jul 1;50(26):3253-3257. doi: 10.1016/j.tetlet.2009.02.018.
Abstract
A variety of heterocyclic alcohols and acetates were coupled with silyl ketene acetals and other π-nucleophiles in the presence of trimethylsilyl trifluoromethanesulfonate to provide an array of substituted β-heteroaryl propionates, including those with contiguous quaternary centers, as well as vinylogs thereof. This reaction also proceeds with high diastereoselectivity when the π-nucleophile bears a chiral auxiliary.
摘要
在三甲基甲硅烷基三氟甲磺酸酯存在下，多种杂环醇和乙酸酯与甲硅烷基烯酮缩醛及其他π-亲核试剂偶联，以提供一系列取代的β-杂芳基丙酸酯，包括具有相邻季碳中心的那些，以及它们的插烯物。当π-亲核试剂带有手性助剂时，该反应也以高非对映选择性进行。
相似文献
1
Synthesis of β-Heteroaryl Propionates via Trapping of Carbocations with π-Nucleophiles.通过用π-亲核试剂捕获碳正离子合成β-杂芳基丙酸酯。
Tetrahedron Lett. 2009 Jul 1;50(26):3253-3257. doi: 10.1016/j.tetlet.2009.02.018.
2
Diastereoselective additions of nucleophiles to alpha-acetoxy ethers using the alpha-(trimethylsilyl)benzyl auxiliary.使用α-（三甲基硅基）苄基助剂将亲核试剂非对映选择性加成到α-乙酰氧基醚上。
Org Lett. 2003 Jun 26;5(13):2367-70. doi: 10.1021/ol0347904.
3
Acyclic stereoselection in the reaction of nucleophilic reagents with chiral N-acyliminium ions generated from N-.亲核试剂与由N-生成的手性N-酰基亚胺离子反应中的非环立体选择性
J Org Chem. 2000 Dec 1;65(24):8277-82. doi: 10.1021/jo001003x.
4
Lewis acid-catalyzed ring-opening reactions of semicyclic N,O-acetals possessing an exocyclic nitrogen atom: mechanistic aspect and application to piperidine alkaloid synthesis.具有环外氮原子的半环状N,O-缩醛的路易斯酸催化开环反应：机理研究及在哌啶生物碱合成中的应用
J Am Chem Soc. 2001 Dec 19;123(50):12510-7. doi: 10.1021/ja0170448.
5
Lewis base activation of Lewis acids: catalytic, enantioselective addition of glycolate-derived silyl ketene acetals to aldehydes.路易斯酸的路易斯碱活化：乙醇酸衍生的甲硅烷基烯酮缩醛对醛的催化对映选择性加成反应
J Org Chem. 2008 Jun 20;73(12):4582-95. doi: 10.1021/jo8006539. Epub 2008 May 28.
6
Catalytic enantioselective aldol reaction to ketones.酮的催化对映选择性羟醛反应。
J Am Chem Soc. 2006 Jun 7;128(22):7164-5. doi: 10.1021/ja061815w.
7
Catalytic enantioselective synthesis of quaternary stereocenters via intermolecular C-acylation of silyl ketene acetals: dual activation of the electrophile and the nucleophile.通过硅基烯酮缩醛的分子间C-酰化反应催化对映选择性合成季碳立体中心：亲电试剂和亲核试剂的双重活化
J Am Chem Soc. 2003 Apr 9;125(14):4050-1. doi: 10.1021/ja028554k.
8
Synthesis of α-Heteroaryl Propionic Esters by Palladium-Catalyzed α-Heteroarylation of Silyl Ketene Acetals.钯催化硅基烯酮缩醛的α-杂芳基化反应合成α-杂芳基丙酸酯。
Org Lett. 2021 Aug 20;23(16):6439-6443. doi: 10.1021/acs.orglett.1c02257. Epub 2021 Aug 9.
9
Expedient synthesis of α-(2-azaheteroaryl) acetates via the addition of silyl ketene acetals to azine-N-oxides.硅基烯酮缩乙酸酯与嗪-N-氧化物加成反应高效合成α-(2-氮杂芳基)乙酸酯。
Org Lett. 2014 Jun 20;16(12):3336-9. doi: 10.1021/ol501359r. Epub 2014 Jun 2.
10
α-Vinylation of Ester Equivalents via Main Group Catalysis for the Construction of Quaternary Centers.通过主族催化实现酯等价物的 α-乙烯基化反应，用于构建季碳中心。
Org Lett. 2023 May 26;25(20):3591-3595. doi: 10.1021/acs.orglett.3c00535. Epub 2023 May 16.
引用本文的文献
1
Experimental Results and Mechanistic Insights on the Reactions of Indolylmethyl Acetates with Soft Carbon Pronucleophiles.吲哚基甲基乙酸酯与软碳亲核前体反应的实验结果及机理见解
ACS Omega. 2024 Jun 17;9(26):28450-28462. doi: 10.1021/acsomega.4c02409. eCollection 2024 Jul 2.
2
Regioselective Reaction of 2-Indolylmethanols with Enamides.2-吲哚甲醇与亚胺的区域选择性反应。
Molecules. 2023 Apr 10;28(8):3341. doi: 10.3390/molecules28083341.
3
Design of an Organocatalytic Asymmetric (4 + 3) Cycloaddition of 2-Indolylalcohols with Dienolsilanes.设计一种有机催化不对称（4 + 3）环加成反应，用于 2-吲哚醇与二烯基硅烷的反应。
J Am Chem Soc. 2022 May 18;144(19):8460-8466. doi: 10.1021/jacs.2c02216. Epub 2022 May 6.
4
Lewis Acid Mediated Vinylogous Additions of Enol Nucleophiles into an α,β-Unsaturated Platinum Carbene.路易斯酸介导的烯醇亲核试剂对α,β-不饱和铂卡宾的乙烯型加成反应
Org Lett. 2016 Jan 4;18(1):64-7. doi: 10.1021/acs.orglett.5b03246. Epub 2015 Dec 14.
5
Concise total synthesis of (±)-actinophyllic acid.（±）-放线菌酸的简洁全合成
Tetrahedron. 2014 Jul 8;70(27-28):4094-4104. doi: 10.1016/j.tet.2014.03.034.
6
Studies toward welwitindolinones: formal syntheses of -methylwelwitindolinone C isothiocyanate and related natural products.对维维菌素的研究：异硫氰酸 - 甲基维维菌素C及相关天然产物的形式合成。
Tetrahedron. 2013 Jul 8;69(27-28):5588-5603. doi: 10.1016/j.tet.2013.03.010.
7
Formal syntheses of naturally occurring welwitindolinones.天然存在的 welwitindolinones 的正规合成。
Org Lett. 2012 Aug 3;14(15):3834-7. doi: 10.1021/ol301424h. Epub 2012 Jul 25.
8
Total synthesis of N-methylwelwitindolinone D isonitrile.N-甲基威尔维啶酮 D 异腈的全合成。
J Am Chem Soc. 2011 Apr 20;133(15):5798-801. doi: 10.1021/ja201834u. Epub 2011 Mar 29.
9
Approaches to N-methylwelwitindolinone C isothiocyanate: facile synthesis of the tetracyclic core.N-甲基威尔维啶酮 C 异硫氰酸酯的方法学研究：四环核心的简便合成。
Org Lett. 2010 Jun 4;12(11):2492-5. doi: 10.1021/ol1006373.
本文引用的文献
1
Organocatalytic asymmetric alkylation of aldehydes by S(N)1-type reaction of alcohols.通过醇的S(N)1型反应实现醛的有机催化不对称烷基化反应。
Angew Chem Int Ed Engl. 2009;48(7):1313-6. doi: 10.1002/anie.200805423.
2
Highly enantioselective Friedel-Crafts reaction of indoles with 2-enoylpyridine 1-oxides catalyzed by chiral pyridine 2,6-bis(5',5'-diphenyloxazoline)-Cu(II) complexes.手性吡啶2,6-双(5',5'-二苯基恶唑啉)-铜(II)配合物催化吲哚与2-烯酰基吡啶1-氧化物的高度对映选择性傅克反应。
Org Lett. 2008 Sep 18;10(18):4121-4. doi: 10.1021/ol8016929. Epub 2008 Aug 23.
3
Dependence of enantioselectivity on the ligand/metal ratio in the asymmetric Michael addition of indole to benzylidene malonates: electronic influence of substrates.吲哚与亚苄基丙二酸酯不对称迈克尔加成反应中对映选择性对配体/金属比例的依赖性：底物的电子影响
Chemistry. 2008;14(24):7259-65. doi: 10.1002/chem.200800508.
4
Catalytic asymmetric Friedel-Crafts alkylation reactions--copper showed the way.催化不对称傅克烷基化反应——铜指明了方向。
Chem Rev. 2008 Aug;108(8):2903-15. doi: 10.1021/cr078372e. Epub 2008 May 24.
5
Chiral phosphoric acid catalyzed enantioselective Friedel-Crafts alkylation of indoles with nitroalkenes: cooperative effect of 3 A molecular sieves.手性磷酸催化吲哚与硝基烯烃的对映选择性傅克烷基化反应：3A分子筛的协同作用
Angew Chem Int Ed Engl. 2008;47(21):4016-8. doi: 10.1002/anie.200800770.
6
Asymmetric Friedel-Crafts alkylation of indoles with methyl (E)-2-oxo-4-aryl-3-butenoates catalyzed by Sc(OTf)3/pybox.三氟甲磺酸钪/吡唑啉酮催化吲哚与(E)-2-氧代-4-芳基-3-丁烯酸甲酯的不对称傅克烷基化反应
Chemistry. 2008;14(12):3630-6. doi: 10.1002/chem.200701908.
7
Asymmetric Brønsted acid catalysis: enantioselective nucleophilic substitutions and 1,4-additions.不对称布朗斯特酸催化：对映选择性亲核取代反应和1,4-加成反应。
Angew Chem Int Ed Engl. 2008;47(3):593-6. doi: 10.1002/anie.200703668.
8
Organocatalytic enantioselective indole alkylations of alpha,beta-unsaturated ketones.α,β-不饱和酮的有机催化对映选择性吲哚烷基化反应
Org Biomol Chem. 2007 Mar 7;5(5):816-21. doi: 10.1039/b616504d. Epub 2007 Jan 19.
9
Rapid synthesis of the N-methylwelwitindolinone skeleton.N-甲基维特吲哚啉酮骨架的快速合成。
Org Lett. 2005 Aug 4;7(16):3421-4. doi: 10.1021/ol051043t.
10
Electrophilic alkylations in neutral aqueous or alcoholic solutions.在中性水溶液或醇溶液中的亲电烷基化反应。
Angew Chem Int Ed Engl. 2004 Oct 11;43(40):5402-5. doi: 10.1002/anie.200460812.
Zotero 插件