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Pure Appl. Chem., 2010, Vol. 82, No. 9, pp. 1797-1812

http://dx.doi.org/10.1351/PAC-CON-09-09-28

Published online 2010-06-28

Intramolecular annulations of donor–acceptor cyclopropanes

Terry P. Lebold and Michael A. Kerr*

Department of Chemistry, The University of Western Ontario, London, Ontario N6A 5B7, Canada

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  • Kishore Gade, Gautam Vibha, Chandrasekaran Srinivasan: Novel synthesis of carbohydrate fused α-amino γ-lactams and glycopeptides by NIS mediated ring opening of donor–acceptor substituted cyclopropanes. Carbohydrate Research 2014, 390, 1. <http://dx.doi.org/10.1016/j.carres.2014.02.022>
  • De Nanteuil Florian, Serrano Eloisa, Perrotta Daniele, Waser Jerome: Dynamic Kinetic Asymmetric [3+2] Annulation Reactions of Aminocyclopropanes. J. Am. Chem. Soc. 2014, 140414115747004. <http://dx.doi.org/10.1021/ja5024578>
  • Cui Bo, Ren Jun, Wang Zhongwen: TfOH-Catalyzed Formal [3 + 2] Cycloaddition of Cyclopropane 1,1-Diesters with Nitriles. J. Org. Chem. 2014, 79, 790. <http://dx.doi.org/10.1021/jo402383a>
  • Mackay William D., Fistikci Meryem, Carris Ryan M., Johnson Jeffrey S.: Lewis Acid Catalyzed (3 + 2)-Annulations of Donor–Acceptor Cyclopropanes and Ynamides. Org. Lett. 2014, 16, 1626. <http://dx.doi.org/10.1021/ol500256n>
  • Ghorai Manas K., Talukdar Ranadeep, Tiwari Deo Prakash: A Route to Highly Functionalized β-Enaminoesters via a Domino Ring-Opening Cyclization/Decarboxylative Tautomerization Sequence of Donor–Acceptor Cyclopropanes with Substituted Malononitriles. Org. Lett. 2014, 140408063623009. <http://dx.doi.org/10.1021/ol5007218>
  • Cavitt Marchello A., Phun Lien H., France Stefan: Intramolecular donor–acceptor cyclopropane ring-opening cyclizations. Chem. Soc. Rev. 2014, 43, 804. <http://dx.doi.org/10.1039/c3cs60238a>
  • Ngo Thien H., Berndt Hülya, Wilsdorf Michael, Lentz Dieter, Reissig Hans-Ulrich: Linear and Cyclic Hybrids of Alternating Thiophene-Amino Acid Units: Synthesis and Effects of Chirality on Conformation and Molecular Packing. Chem. Eur. J. 2013, 19, 15155. <http://dx.doi.org/10.1002/chem.201302143>
  • Kong Han Il, Gill Monica A., Hrdina Amy H., Crichton Jennifer E., Manthorpe Jeffrey M.: Reactivity of α-trifluoromethanesulfonyl esters, amides and ketones: Decarboxylative allylation, methylation, and enol formation. Journal of Fluorine Chemistry 2013, 153, 151. <http://dx.doi.org/10.1016/j.jfluchem.2013.03.020>
  • Sun Yongxian, Yang Gaosheng, Shen Yue, Hua Zan, Chai Zhuo: Stereoselective cyclopropanation of α-bromochalcone with diethyl malonate promoted by K2CO3. Tetrahedron 2013, 69, 2733. <http://dx.doi.org/10.1016/j.tet.2013.02.011>
  • Yang Gaosheng, Sun Yongxian, Shen Yue, Chai Zhuo, Zhou Shuangliu, Chu Jiang, Chai Jun: cis-2,3-Disubstituted Cyclopropane 1,1-Diesters in [3 + 2] Annulations with Aldehydes: Highly Diastereoselective Construction of Densely Substituted Tetrahydrofurans. J. Org. Chem. 2013, 78, 5393. <http://dx.doi.org/10.1021/jo400554a>
  • Dhakal Ramesh C., Dieter R. Karl: Regio- and Stereocontrol in the Michael-Initiated Ring-Closure Reactions of γ,δ-Epoxy-α,β-unsaturated Esters, Ketones, Sulfones, and Amides. J. Org. Chem. 2013, 78, 12426. <http://dx.doi.org/10.1021/jo402075d>
  • Haubenreisser Stefan, Hensenne Peter, Schröder Sebastian, Niggemann Meike: The Alkynyl Moiety as a Donor for Donor–Acceptor Cyclopropanes. Org. Lett. 2013, 15, 2262. <http://dx.doi.org/10.1021/ol400809n>
  • Wales Steven M., Walker Morgan M., Johnson Jeffrey S.: Asymmetric Synthesis of Indole Homo-Michael Adducts via Dynamic Kinetic Friedel–Crafts Alkylation with Cyclopropanes. Org. Lett. 2013, 15, 2558. <http://dx.doi.org/10.1021/ol4010646>
  • Wang Peng, Liao Saihu, Zhu Jian-Bo, Tang Yong: Iron-Catalyzed Three-Component Reaction: Multiple C–C Bond Cleavages and Reorganizations. Org. Lett. 2013, 15, 3606. <http://dx.doi.org/10.1021/ol4014552>
  • Ghorai Manas K., Talukdar Ranadeep, Tiwari Deo Prakash: An efficient synthetic route to carbocyclic enaminonitriles via Lewis acid catalysed domino-ring-opening-cyclisation (DROC) of donor–acceptor cyclopropanes with malononitrile. Chem. Commun. 2013, 49, 8205. <http://dx.doi.org/10.1039/c3cc44533j>
  • Cheng Donghao, Huang Deshun, Shi Yian: Synergistic effect of additives on cyclopropanation of olefins. Org. Biomol. Chem. 2013, 11, 5588. <http://dx.doi.org/10.1039/c3ob40751a>
  • Sun Yongxian, Yang Gaosheng, Chai Zhuo, Mu Xiaolong, Chai Jun: AlCl3-promoted [3 + 2] annulation of cis-2,3-disubstituted cyclopropane 1,1-diesters with isothiocyanates: stereoselective synthesis of densely substituted 2-iminodihydrothiophenes. Org. Biomol. Chem. 2013, 11, 7859. <http://dx.doi.org/10.1039/c3ob41678j>
  • Deng Chao, Wang Li-Jia, Zhu Jun, Tang Yong: A Chiral Cagelike Copper(I) Catalyst for the Highly Enantioselective Synthesis of 1,1-Cyclopropane Diesters. Angew. Chem. 2012, 124, 11788. <http://dx.doi.org/10.1002/ange.201206376>
  • Deng Chao, Wang Li-Jia, Zhu Jun, Tang Yong: A Chiral Cagelike Copper(I) Catalyst for the Highly Enantioselective Synthesis of 1,1-Cyclopropane Diesters. Angew. Chem. Int. Ed. 2012, 51, 11620. <http://dx.doi.org/10.1002/anie.201206376>
  • Xia Xiao-Feng, Song Xian-Rong, Liu Xue-Yuan, Liang Yong-Min: Lewis Acid-Catalyzed Intramolecular [3+2] Cycloaddition of Cyclopropane 1,1-Diesters with Alkynes for the Synthesis of Cyclopenta[c ]chromene Skeletons. Chem. Asian J. 2012, 7, 1538. <http://dx.doi.org/10.1002/asia.201200104>
  • Qu Jian-Ping, Liang Yong, Xu Hao, Sun Xiu-Li, Yu Zhi-Xiang, Tang Yong: Highly Diastereoselective Construction of Fused Carbocycles from Cyclopropane-1,1-dicarboxylates and Cyclic Enol Silyl Ethers: Scope, Mechanism, and Origin of Diastereoselectivity. Chemistry A European Journal 2012, 18, 2196. <http://dx.doi.org/10.1002/chem.201103495>
  • Benfatti Fides, de Nanteuil Florian, Waser Jérôme: Catalytic Enantiospecific [3+2] Annulation of Aminocyclopropanes with Ketones. Chemistry A European Journal 2012, 18, 4844. <http://dx.doi.org/10.1002/chem.201103971>
  • Gladow Daniel, Reissig Hans-Ulrich: Synthesis of Perfluoroalkyl-Substituted γ -Lactones and 4,5-Dihydropyridazin-3(2H )-ones via DonorAcceptor Cyclopropanes. HCA 2012, 95, 1818. <http://dx.doi.org/10.1002/hlca.201200413>
  • Zhou You-Yun, Wang Li-Jia, Li Jun, Sun Xiu-Li, Tang Yong: Side-Arm-Promoted Highly Enantioselective Ring-Opening Reactions and Kinetic Resolution of Donor–Acceptor Cyclopropanes with Amines. J. Am. Chem. Soc. 2012, 134, 9066. <http://dx.doi.org/10.1021/ja302691r>
  • Trost Barry M., Morris Patrick J., Sprague Simon J.: Palladium-Catalyzed Diastereo- and Enantioselective Formal [3 + 2]-Cycloadditions of Substituted Vinylcyclopropanes. J. Am. Chem. Soc. 2012, 134, 17823. <http://dx.doi.org/10.1021/ja309003x>
  • Ngo Thien H., Berndt Hülya, Lentz Dieter, Reissig Hans-Ulrich: Linear and Cyclic Amides with a Thiophene Backbone: Ultrasound-Promoted Synthesis and Crystal Structures. J. Org. Chem. 2012, 77, 9676. <http://dx.doi.org/10.1021/jo3017605>
  • Benfatti Fides, Nanteuil Florian de, Waser Jérôme: Iron-Catalyzed [3 + 2] Annulation of Aminocyclopropanes with Aldehydes: Stereoselective Synthesis of Aminotetrahydrofurans. Org Lett 2012, 14, 386. <http://dx.doi.org/10.1021/ol203144v>
  • Cornwall Richard G., Wong O. Andrea, Du Haifeng, Ramirez Thomas A., Shi Yian: A novel class of tunable cyclopropanation reagents (RXZnCH2Y) and their synthetic applications. Org. Biomol. Chem. 2012, 10, 5498. <http://dx.doi.org/10.1039/c2ob25481f>
  • Okado Ryohei, Nowaki Aya, Matsuo Jun-ichi, Ishibashi Hiroyuki: Formal [4+2] Cycloaddition of di-tert-Butyl 2-Ethoxycyclobutane-1,1-dicarboxylate with Ketones or Aldehydes and Tandem Lactonization. Chemical Pharmaceutical Bulletin 2012, 60, 21. <http://dx.doi.org/10.1248/cpb.60.21>
  • Ivanova Olga A., Budynina Ekaterina M., Chagarovskiy Alexey O., Kaplun Alexey E., Trushkov Igor V., Melnikov Mikhail Ya.: Lewis Acid-Catalyzed [3+4] Annulation of 2-(Heteroaryl)- cyclopropane-1,1-dicarboxylates with Cyclopentadiene. Synth Catal 2011, 353, 1125. <http://dx.doi.org/10.1002/adsc.201000783>
  • de Nanteuil Florian, Waser Jérôme: Catalytic [3+2] Annulation of Aminocyclopropanes for the Enantiospecific Synthesis of Cyclopentylamines. angew chemie 2011, 123, 12281. <http://dx.doi.org/10.1002/ange.201106255>
  • de Nanteuil Florian, Waser Jérôme: Catalytic [3+2] Annulation of Aminocyclopropanes for the Enantiospecific Synthesis of Cyclopentylamines. Angew Chem Int E 2011, 50, 12075. <http://dx.doi.org/10.1002/anie.201106255>
  • De Simone Filippo, Saget Tanguy, Benfatti Fides, Almeida Sofia, Waser Jérôme: Formal Homo-Nazarov and Other Cyclization Reactions of Activated Cyclopropanes. Chemistry A European Journal 2011, 17, 14527. <http://dx.doi.org/10.1002/chem.201102583>
  • Lebold Terry P., Kerr Michael A.: ChemInform Abstract: Intramolecular Annulations of Donor-Acceptor Cyclopropanes. ChemInform 2011, 42, no. <http://dx.doi.org/10.1002/chin.201109260>
  • Mel’nikov Mikhail Ya., Budynina Ekaterina M., Ivanova Olga A., Trushkov Igor V.: Recent advances in ring-forming reactions of donor–acceptor cyclopropanes. MENDELEEV COMMUN 2011, 21, 293. <http://dx.doi.org/10.1016/j.mencom.2011.11.001>
  • Kong Han Il, Crichton Jennifer E., Manthorpe Jeffrey M.: Stereoselective synthesis of ambiphilic alkenes via regioselective methylation of α-trifluoromethanesulfonyl carbonyl compounds with trimethylsilyldiazomethane. Tetrahetron Lett 2011, 52, 3714. <http://dx.doi.org/10.1016/j.tetlet.2011.05.015>
  • Jenkins Aireal D., Herath Ananda, Song Minsoo, Montgomery John: Synthesis of Cyclopentenols and Cyclopentenones via Nickel-Catalyzed Reductive Cycloaddition. J Ann Chem Soc 2011, 133, 14460. <http://dx.doi.org/10.1021/ja206722t>