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Pure Appl. Chem., 2010, Vol. 82, No. 3, pp. 657-668

http://dx.doi.org/10.1351/PAC-CON-09-10-17

Published online 2010-02-18

Gold-catalyzed synthesis of N,O-heterocycles

A. Stephen K. Hashmi

Institute of Organic Chemistry, Ruprecht-Karls-University Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany

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  • Yu Yong-Fei, Shu Chao, Shen Cang-Hai, Li Tian-Yi, Ye Long-Wu: Gold-Catalyzed Tandem Cycloisomerization and Dimerization of Chiral Homopropargyl Sulfonamides. Chem. Asian J. 2013, 8, 2920. <http://dx.doi.org/10.1002/asia.201301058>
  • Malhotra Deepika, Liu Le-Ping, Mashuta Mark S., Hammond G. B.: Gold-Catalyzed Annulations of 2-Alkynyl Benzaldehydes with Vinyl Ethers: Synthesis of Dihydronaphthalene, Isochromene, and Bicyclo[2.2.2]octane Derivatives. Chem. Eur. J. 2013, 19, 4043. <http://dx.doi.org/10.1002/chem.201203841>
  • Abbiati Giorgio, Marinelli Fabio, Rossi Elisabetta, Arcadi Antonio: Synthesis of Indole Derivatives from 2-Alkynylanilines by Means of Gold Catalysis. Isr. J. Chem. 2013, 53, 856. <http://dx.doi.org/10.1002/ijch.201300040>
  • Tran-Dubé Michelle, Johnson Sarah, McAlpine Indrawan: A two-step, one-pot procedure using acid chlorides and propargyl amines to form tri-substituted oxazoles via gold-catalyzed cyclization. Tetrahedron Letters 2013, 54, 259. <http://dx.doi.org/10.1016/j.tetlet.2012.11.013>
  • Bouvet Sébastien, Moreau Xavier, Coeffard Vincent, Greck Christine: Synthesis of Enantioenriched Aza-Proline Derivatives through Gold(I)-Catalyzed Cyclization of Chiral α-Hydrazino Esters. J. Org. Chem. 2013, 78, 427. <http://dx.doi.org/10.1021/jo302320v>
  • Shu Chao, Liu Meng-Qi, Wang Shan-Shan, Li Long, Ye Long-Wu: Gold-Catalyzed Oxidative Cyclization of Chiral Homopropargyl Amides: Synthesis of Enantioenriched γ-Lactams. J. Org. Chem. 2013, 78, 3292. <http://dx.doi.org/10.1021/jo400127x>
  • Yu Xinzhang, Xin Xiaoyi, Wan Boshun, Li Xingwei: Base-Catalyzed Cyclization of N-Sulfonyl Propargylamides to Sulfonylmethyl-Substituted Oxazoles via Sulfonyl Migration. J. Org. Chem. 2013, 78, 4895. <http://dx.doi.org/10.1021/jo4004635>
  • Hashmi A. Stephen K., Ghanbari Mohammad, Rudolph Matthias, Rominger Frank: Combining Gold and Palladium Catalysis: One-Pot Access to Pentasubstituted Arenes from Furan-Yne and En-Diyne Substrates. Chem. Eur. J. 2012, 18, 8113. <http://dx.doi.org/10.1002/chem.201200091>
  • Usanov Dmitry L., Naodovic Marina, Brasholz Malte, Yamamoto Hisashi: Gold(I)-Catalyzed Cyclodehydration Enabled by the Triisopropylsilyl Group: A Synthetically Versatile Methodology. HCA 2012, 95, 1773. <http://dx.doi.org/10.1002/hlca.201200176>
  • Usanov Dmitry L., Yamamoto Hisashi: Formation of Five- and Seven-Membered Rings Enabled by the Triisopropylsilyl Auxiliary Group. Org Lett 2012, 14, 414. <http://dx.doi.org/10.1021/ol203209b>
  • Gierz Verena, Seyboldt Alexander, Maichle-Mössmer Cäcilia, Törnroos Karl W., Speidel Michael T., Speiser Bernd, Eichele Klaus, Kunz Doris: Dinuclear Coinage-Metal Complexes of Bis(NHC) Ligands: Structural Features and Dynamic Behavior of a Cu–Cu Complex. Organometallics 2012, 31, 7893. <http://dx.doi.org/10.1021/om300544g>
  • Falletta Ermelinda, Rossi Michele, Pina Cristina Della: Update on selective oxidation using gold. Chemical Society Review 2012, 41, 350. <http://dx.doi.org/10.1039/c1cs15089h>
  • Huang Genping, Xu Liang, Xia Yuanzhi, Cheng Bing: Mechanism of the N-protecting group dependent annulations of 3-aryloxy alkynyl indoles under gold catalysis: a computational study. Biomol Chem 2012, 10, 4417. <http://dx.doi.org/10.1039/c2ob25316j>
  • Yeom Hyun-Suk, So Eunsu, Shin Seunghoon: Gold-Catalyzed Synthesis of 3-Pyrrolidinones and Nitrones from N-Sulfonyl Hydroxylamines via Oxygen-Transfer Redox and 1,3-Sulfonyl Migration. Chem Eur J 2011, 17, 1764. <http://dx.doi.org/10.1002/chem.201002863>
  • Hashmi A. Stephen K., Schuster Andreas M., Litters Sebastian, Rominger Frank, Pernpointner Markus: Gold Catalysis: 1,3-Oxazines by Cyclisation of Allene Amides. Chem Eur J 2011, 17, 5661. <http://dx.doi.org/10.1002/chem.201100132>
  • Hashmi A. Stephen K., Molinari Lise, Rominger Frank, Oeser Thomas: Gold Catalysis: Products and Intermediates Obtained from N-Propargylcarboxamides Bearing Additional Substituents on Nitrogen. Eur J Org Chem 2011, 2011, 2256. <http://dx.doi.org/10.1002/ejoc.201100179>
  • Fernández-García Jesús Manuel, Fernández-Rodríguez Manuel Á., Aguilar Enrique: Catalytic Intermolecular Hetero-Dehydro-Diels–Alder Cycloadditions: Regio- and Diasteroselective Synthesis of 5,6-Dihydropyridin-2-ones. Org Lett 2011, 13, 5172. <http://dx.doi.org/10.1021/ol202046y>
  • Rudolph Matthias, Hashmi A. Stephen K.: Heterocycles from gold catalysis. Chem Commun 2011, 47, 6536. <http://dx.doi.org/10.1039/c1cc10780a>
  • Heugebaert Thomas S. A., Vervaecke Leander P. D., Stevens Christian V.: Gold(iii) chloride catalysed synthesis of 5-alkylidene-dihydrothiazoles. Org Biomol Chem 2011, 9, 4791. <http://dx.doi.org/10.1039/c1ob05509g>
  • Hashmi A. Stephen K.: ChemInform Abstract: Gold-Catalyzed Synthesis of N,O-Heterocycles. ChemInform 2010, 41, no. <http://dx.doi.org/10.1002/chin.201035247>
  • Hashmi A. Stephen K.: New pathways in the gold-catalyzed cycloisomerization of furanynes. Pure and App Chemis 2010, 1. <http://dx.doi.org/10.1351/PAC-CON-09-10-34>