Regioselective Reaction of 2-Indolylmethanols with Enamides

A highly regioselective reaction of 2-indolylmethanols with enamides has been developed at room temperature by using AlCl3 as a catalyst. A wide range of hybrids (40 examples) of indoles and enamides were obtained in moderate to good yields (up to 98% yield). This transformation represents the efficient way to introduce biologically important indoles and enamides skeleton into structurally complex hybrids.

[1]  V. Soloshonok,et al.  Catalytic Asymmetric α-Functionalization of α-Branched Aldehydes , 2023, Molecules.

[2]  Ping Wu,et al.  Design and Application of m ‐Hydroxybenzyl Alcohols in Regioselective (3+3) Cycloadditions of 2‐Indolymethanols , 2022, Chinese Journal of Chemistry.

[3]  Fabio Pesciaioli,et al.  Synergistic Strategies in Aminocatalysis , 2022, Chemistry.

[4]  Limin Wang,et al.  PFOA‐Catalyzed Regioselective Alkylation of Indolylmethanols with 2‐Alkylazaarenes** , 2022, ChemistrySelect.

[5]  X. Dai,et al.  Synthesis of C3-functionalized indole derivatives via Brønsted acid-catalyzed regioselective arylation of 2-indolylmethanols with guaiazulene. , 2022, Organic & biomolecular chemistry.

[6]  Limin Wang,et al.  La(OTf)3 facilitated self-condensation of 2-indolylmethanol: construction of highly substituted indeno[1,2-b]indoles. , 2021, Organic & biomolecular chemistry.

[7]  Shiqiang Wei,et al.  Construction of a spiro[pyrazolone-4,2'-pyridoindole] scaffold via a [3 + 3] cycloaddition of 2-indolylmethanol with a 4-aminopyrazolone-derived azomethine ylide. , 2021, Organic & biomolecular chemistry.

[8]  Zhi‐Qiang Zhu,et al.  Formal (3 + 4)-Annulation of Propargylic p-Quinone Methides with 2-Indolylmethanols: Synthesis of Polysubstituted Indole-Fused Oxepines. , 2021, The Journal of organic chemistry.

[9]  Xiaoan Wen,et al.  Synthesis of indole-fused scaffolds via [3+3] cyclization reaction of 2-indolylmethanols with quinone imines , 2021 .

[10]  Jikai Liu,et al.  [3 + 2] Cycloaddition of Nitrile Imines with Enamides: An Approach to Functionalized Pyrazolines and Pyrazoles. , 2020, The Journal of organic chemistry.

[11]  Kai Zhao,et al.  Regio- and stereoselective C(sp2)–H acylation of enamides with aldehydes via transition-metal-free photoredox catalysis , 2020 .

[12]  F. Shi,et al.  Axially Chiral Aryl‐Alkene‐Indole Framework: A Nascent Member of the Atropisomeric Family and Its Catalytic Asymmetric Construction , 2020 .

[13]  Yu Zhang,et al.  Temperature-controlled regioselective thiolation of 2-indolylmethanols under aqueous micellar conditions , 2020 .

[14]  Ting Guan,et al.  Stereoselective C(sp2)-H Alkylation of Enamides with Unactivated Aliphatic Carboxylic Acids via Decarboxylative Cross-Coupling Reactions. , 2019, Organic letters.

[15]  Mi Yan,et al.  Indole: A privileged scaffold for the design of anti-cancer agents. , 2019, European journal of medicinal chemistry.

[16]  Zeyu Zhang,et al.  Photoredox-catalyzed stereoselective alkylation of enamides with N-hydroxyphthalimide esters via decarboxylative cross-coupling reactions† †Electronic supplementary information (ESI) available. CCDC 1874601. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c9sc030 , 2019, Chemical science.

[17]  Kai Zhao,et al.  Direct C( sp 2 )‐H Arylsulfonylation of Enamides via Iridium(III)‐Catalyzed Insertion of Sulfur Dioxide with Aryldiazonium Tetrafluoroborates , 2019, Advanced Synthesis & Catalysis.

[18]  Zeyu Zhang,et al.  Regioselective and Stereoselective Difluoromethylation of Enamides with Difluoromethyltriphenylphosphonium Bromide via Photoredox Catalysis. , 2019, Organic letters.

[19]  F. Shi,et al.  Catalytic Asymmetric (4+3) Cyclizations of In Situ Generated ortho-Quinone Methides with 2-Indolylmethanols. , 2019, Angewandte Chemie.

[20]  Guang-Jian Mei,et al.  Design and Catalytic Asymmetric Construction of Axially Chiral 3,3'-Bisindole Skeletons. , 2019, Angewandte Chemie.

[21]  Kai Zhao,et al.  Cu(OTf)2-mediated C(sp2)–H arylsulfonylation of enamides via the insertion of sulfur dioxide , 2019, Organic Chemistry Frontiers.

[22]  Jie Wu,et al.  Brønsted acid-catalysed regiodivergent phosphorylation of 2-indolylmethanols to synthesize benzylic site or C3-phosphorylated indole derivatives. , 2018, Organic & biomolecular chemistry.

[23]  Guang-Jian Mei,et al.  Catalytic enantioselective and regioselective substitution of 2,3-indolyldimethanols with enaminones , 2018 .

[24]  Guang-Jian Mei,et al.  A catalytic asymmetric interrupted Nazarov-type cyclization of 2-indolylmethanols with cyclic enaminones. , 2018, Organic & biomolecular chemistry.

[25]  Lei Yu,et al.  Regioselective [3+3] Cyclization of 2-Indolymethanols with Vinylcyclopropanes via Metal Catalysis , 2018, Advanced Synthesis & Catalysis.

[26]  S. Ji,et al.  Ag(I)-Promoted Dehydroxylation and Site-Selective 1,7-Disulfonylation of Diaryl(1 H-indol-2-yl)methanols. , 2018, The Journal of organic chemistry.

[27]  Y. Wan,et al.  Application of 7‐Indolylmethanols in Catalytic Asymmetric Arylations with Tryptamines: Enantioselective Synthesis of 7‐indolylmethanes , 2018 .

[28]  Guang-Jian Mei,et al.  Cooperative Catalysis-Enabled Asymmetric α-Arylation of Aldehydes Using 2-Indolylmethanols as Arylation Reagents. , 2018, The Journal of organic chemistry.

[29]  Limin Wang,et al.  Lewis Acid-Controlled Regioselective Phosphorylation of 2-Indolylmethanols with Diarylphosphine Oxides: Synthesis of Highly Substituted Indoles. , 2018, The Journal of organic chemistry.

[30]  Y. Wan,et al.  Direct C3-arylations of 2-indolylmethanols with tryptamines and tryptophols via an umpolung strategy. , 2018, Organic & biomolecular chemistry.

[31]  Y. Wan,et al.  Enantioselective Construction of Cyclopenta[b]indole Scaffolds via the Catalytic Asymmetric [3 + 2] Cycloaddition of 2-Indolylmethanols with p-Hydroxystyrenes. , 2017, The Journal of organic chemistry.

[32]  Lei Yu,et al.  Brønsted Acid Catalyzed C3-Alkylation of 2-Indolylmethanols with Azlactones via an Umpolung Strategy , 2017, Synthesis.

[33]  F. Shi,et al.  Enantioselective Direct α-Arylation of Pyrazol-5-ones with 2-Indolylmethanols via Organo-Metal Cooperative Catalysis. , 2017, Organic letters.

[34]  Guang-Jian Mei,et al.  Substrate-Controlled Regioselective Arylations of 2-Indolylmethanols with Indoles: Synthesis of Bis(indolyl)methane and 3,3'-Bisindole Derivatives. , 2017, The Journal of organic chemistry.

[35]  Guang-Jian Mei,et al.  Design and Enantioselective Construction of Axially Chiral Naphthyl-Indole Skeletons. , 2017, Angewandte Chemie.

[36]  C. Schneider,et al.  Brønsted Acid Catalyzed Addition of Enamides to ortho-Quinone Methide Imines-An Efficient and Highly Enantioselective Synthesis of Chiral Tetrahydroacridines. , 2016, Angewandte Chemie.

[37]  F. Shi,et al.  Brønsted acid-catalyzed regioselective reactions of 2-indolylmethanols with cyclic enaminone and anhydride leading to C3-functionalized indole derivatives. , 2016, Organic & biomolecular chemistry.

[38]  Xiaomei Zhang,et al.  Highly enantioselective [3+2] coupling of cyclic enamides with quinone monoimines promoted by a chiral phosphoric acid. , 2016, Chemical communications.

[39]  G. Masson,et al.  Chiral Phosphoric Acid Catalyzed [3 + 2] Cycloaddition and Tandem Oxidative [3 + 2] Cycloaddition: Asymmetric Synthesis of Substituted 3-Aminodihydrobenzofurans. , 2016, Organic letters.

[40]  Liang Zhao,et al.  Catalytic Asymmetric Tandem Reaction of Tertiary Enamides: Expeditious Synthesis of Pyrrolo[2,1-a]isoquinoline Alkaloid Derivatives. , 2016, Angewandte Chemie.

[41]  徐鲁斌,et al.  基于吲哚-3-基甲醇不对称合成光学活性吲哚衍生物研究进展 , 2016 .

[42]  Liang Zhao,et al.  Synthesis of 2,3-Dihydro-1H-azepine and 1H-Azepin-2(3H)-one Derivatives From Intramolecular Condensation between Stable Tertiary Enamides and Aldehydes. , 2015, The Journal of organic chemistry.

[43]  Fu‐She Han,et al.  Organocatalytic asymmetric reaction of indol-2-yl carbinols with enamides: synthesis of chiral 2-indole-substituted 1,1-diarylalkanes. , 2015, Chemical communications.

[44]  Xiaodong Tang,et al.  Chiral phosphoric acid catalyzed enantioselective decarboxylative alkylation of β-keto acids with 3-hydroxy-3-indolyloxindoles. , 2015, Organic letters.

[45]  Zhi‐Lei Guo,et al.  The direct asymmetric alkylation of α-amino aldehydes with 3-indolylmethanols by enamine catalysis. , 2014, Organic letters.

[46]  Xin Li,et al.  Highly diastereo- and enantioselective construction of a spiro[cyclopenta[b]indole-1,3'-oxindole] scaffold via catalytic asymmetric formal [3+2] cycloadditions. , 2014, Chemical communications.

[47]  Liang Wang,et al.  Alkylideneindoleninium Ions and Alkylideneindolenines: Key Intermediates for the Asymmetric Synthesis of 3-Indolyl Derivatives , 2014 .

[48]  Jian Zhou,et al.  Catalytic functionalization of tertiary alcohols to fully substituted carbon centres. , 2014, Organic & biomolecular chemistry.

[49]  Biao Xu,et al.  Catalytic asymmetric direct α-alkylation of amino esters by aldehydes via imine activation , 2014 .

[50]  E. Carreira,et al.  Iridium-catalyzed enantioselective allylic vinylation. , 2013, Journal of the American Chemical Society.

[51]  X. Pannecoucke,et al.  Copper-catalyzed direct arylation of cyclic enamides using diaryliodonium salts. , 2013, Organic letters.

[52]  H. Neumann,et al.  Synthesis of heterocycles via palladium-catalyzed carbonylations. , 2013, Chemical reviews.

[53]  Fu‐She Han,et al.  Al-catalyzed facile construction of quaternary C-C bonds by the allylic substitution of tertiary alcohols: a concise and formal synthesis of (±)-mersicarpine. , 2012, Chemistry.

[54]  Yungui Peng,et al.  The direct asymmetric α alkylation of ketones by Brønsted acid catalysis. , 2012, Angewandte Chemie.

[55]  María Sánchez-Roselló,et al.  From 2000 to mid-2010: a fruitful decade for the synthesis of pyrazoles. , 2011, Chemical reviews.

[56]  Yong‐Gui Zhou,et al.  Dehydration triggered asymmetric hydrogenation of 3-(α-hydroxyalkyl)indoles , 2011 .

[57]  Zhenjie Zhang,et al.  Chiral Brønsted acid catalyzed pinacol rearrangement. , 2010, Angewandte Chemie.

[58]  M. Hamann,et al.  Marine indole alkaloids: potential new drug leads for the control of depression and anxiety. , 2010, Chemical reviews.

[59]  A. Palmieri,et al.  Synthesis of 3-substituted indoles via reactive alkylideneindolenine intermediates. , 2010, Organic & biomolecular chemistry.

[60]  M. Bandini,et al.  Catalytic functionalization of indoles in a new dimension. , 2009, Angewandte Chemie.

[61]  S. Martin,et al.  Synthesis of β-Heteroaryl Propionates via Trapping of Carbocations with π-Nucleophiles. , 2009, Tetrahedron letters.

[62]  Pascal Retailleau,et al.  Chiral Brønsted acid-catalyzed enantioselective three-component Povarov reaction. , 2009, Journal of the American Chemical Society.

[63]  L. Zoli,et al.  Organocatalytic asymmetric alkylation of aldehydes by S(N)1-type reaction of alcohols. , 2009, Angewandte Chemie.

[64]  Jeffrey T. Kuethe,et al.  Practical methodologies for the synthesis of indoles. , 2006, Chemical reviews.

[65]  Alexander Deiters,et al.  Synthesis of oxygen- and nitrogen-containing heterocycles by ring-closing metathesis. , 2004, Chemical reviews.