User menu

Copper-catalyzed vinylsilane allylation

Bibliographic reference Cornelissen, Loïc ; Vercruysse, Sébastien ; Sanhadji, A. ; Riant, Olivier. Copper-catalyzed vinylsilane allylation. In: European Journal of Organic Chemistry, Vol. 2014, no.1, p. 35-38 (2014)
Permanent URL http://hdl.handle.net/2078.1/137170
  1. Fleming Ian, Barbero Asuncion, Walter David, Stereochemical Control in Organic Synthesis Using Silicon-Containing Compounds, 10.1021/cr941074u
  2. Curtis-Long Marcus J., Aye Yimon, Vinyl-, Propargyl-, and Allenylsilicon Reagents in Asymmetric Synthesis: A Relatively Untapped Resource of Environmentally Benign Reagents, 10.1002/chem.200900337
  3. Synthesis 2012 44
  4. Barbero Asunción, Pulido Francisco J., Allylsilanes and Vinylsilanes from Silylcupration of Carbon−Carbon Multiple Bonds:  Scope and Synthetic Applications, 10.1021/ar0400490
  5. Berthon-Gelloz Guillaume, Schumers Jean-Marc, De Bo Guillaume, Markó István E., Highly β-(E)-Selective Hydrosilylation of Terminal and Internal Alkynes Catalyzed by a (IPr)Pt(diene) Complex, 10.1021/jo800411e
  6. De Bo Guillaume, Berthon-Gelloz Guillaume, Tinant Bernard, Markó István E., Hydrosilylation of Alkynes Mediated byN-Heterocyclic Carbene Platinum(0) Complexes, 10.1021/om050866j
  7. Chatterjee Arnab K., Morgan John P., Scholl Matthias, Grubbs Robert H., Synthesis of Functionalized Olefins by Cross and Ring-Closing Metatheses, 10.1021/ja9939744
  8. Pietraszuk Cezary, Fischer Helmut, Kujawa Małgorzata, Marciniec Bogdan, Cross-metathesis of vinylsilanes with olefins in the presence of Grubbs’ catalyst, 10.1016/s0040-4039(00)02201-2
  9. Miyake Yoshihiro, Isomura Eigo, Iyoda Masahiko, Selective Hydrosilylation of 1-Alkynes Using Iridium Catalyst with Biphosphinine Ligand, 10.1246/cl.2006.836
  10. Trost Barry M., Ball Zachary T., Alkyne Hydrosilylation Catalyzed by a Cationic Ruthenium Complex:  Efficient and General Trans Addition, 10.1021/ja0528580
  11. Chem. Soc. Rev. 2011 40
  12. Kabalka George W., Al-Masum Mohammad, Microwave-Enhanced Palladium-Catalyzed Cross-Coupling Reactions of Potassium Vinyltrifluoroborates and Allyl Acetates:  A New Route to 1,4-Pentadienes, 10.1021/ol051955v
  13. Dey Raju, Chattopadhyay Kalicharan, Ranu Brindaban C., Palladium(0) Nanoparticle Catalyzed Cross-Coupling of Allyl Acetates and Aryl and Vinyl Siloxanes, 10.1021/jo802214m
  14. Alacid Emilio, Nájera Carmen, Palladium-Catalyzed Cross-Coupling Reactions of Potassium Alkenyltrifluoroborates with Organic Halides in Aqueous Media†, 10.1021/jo802356n
  15. Taguchi Haruhiko, Miyashita Hiroko, Tsubouchi Akira, Takeda Takeshi, First anionic silyl migration from sp2carbon to carbonyl oxygen. Stereospecific allylation of (Z)-β-trimethylsilyl-α,β-unsaturated ketones, 10.1039/b207325k
  16. Tsubouchi Akira, Onishi Kotaro, Takeda Takeshi, Stereoselective Preparation of 1-Siloxy-1-alkenylcopper Species by 1,2-Csp2-to-O Silyl Migration of Acylsilanes, 10.1021/ja0658822
  17. Tsubouchi Akira, Matsuda Hiroko, Kira Takashiro, Takeda Takeshi, Silyl Migration in Conjunction with Substitution on Silicon in Copper(I)t-Butoxide-promoted Coupling betweeno-Silylphenyl Ketones and Organic Halides, 10.1246/cl.2009.1180
  18. Tsubouchi Akira, Enatsu Shouko, Kanno Ryo, Takeda Takeshi, Complete Regio- and Stereoselective Construction of Highly Substituted Silyl Enol Ethers by Three-Component Coupling, 10.1002/ange.201003152
  19. Tomita Daisuke, Wada Reiko, Kanai Motomu, Shibasaki Masakatsu, Enantioselective Alkenylation and Phenylation Catalyzed by a Chiral CuF Complex, 10.1021/ja0507362
  20. Lee Kang-sang, Hoveyda Amir H., Monodentate Non-C2-symmetric ChiralN-Heterocyclic Carbene Complexes for Enantioselective Synthesis. Cu-Catalyzed Conjugate Additions of Aryl- and Alkenylsilylfluorides to Cyclic Enones, 10.1021/jo900589x
  21. Alexakis A., Bäckvall J. E., Krause N., Pàmies O., Diéguez M., Enantioselective Copper-Catalyzed Conjugate Addition and Allylic Substitution Reactions, 10.1021/cr0683515
  22. Falciola Caroline A., Alexakis Alexandre, Copper-Catalyzed Asymmetric Allylic Alkylation, 10.1002/ejoc.200800025
  23. Harutyunyan Syuzanna R., den Hartog Tim, Geurts Koen, Minnaard Adriaan J., Feringa Ben L., Catalytic Asymmetric Conjugate Addition and Allylic Alkylation with Grignard Reagents, 10.1021/cr068424k
  24. Alexakis Alexandre, Malan Christophe, Lea Louise, Benhaim Cyril, Fournioux Xavier, Enantioselective Copper-Catalyzed SN2′ Substitution with Grignard Reagents, 10.1055/s-2001-14626
  25. Li Hailing, Alexakis Alexandre, Enyne Chlorides: Substrates for Copper-Catalyzed Asymmetric Allylic Alkylation, 10.1002/ange.201107129
  26. Hornillos Valentín, Pérez Manuel, Fañanás-Mastral Martín, Feringa Ben L., Cu-Catalyzed Asymmetric Allylic Alkylation of Phosphonates and Phosphine Oxides with Grignard Reagents, 10.1002/chem.201204364
  27. Hornillos Valentín, Pérez Manuel, Fañanás-Mastral Martín, Feringa Ben L., Copper-Catalyzed Enantioselective Allyl–Allyl Cross-Coupling, 10.1021/ja312487r
  28. Fañanás-Mastral Martín, Pérez Manuel, Bos Pieter H., Rudolph Alena, Harutyunyan Syuzanna R., Feringa Ben L., Enantioselective Synthesis of Tertiary and Quaternary Stereogenic Centers: Copper/Phosphoramidite-Catalyzed Allylic Alkylation with Organolithium Reagents, 10.1002/ange.201107840
  29. Dübner Frank, Knochel Paul, Kupfer(I)-katalysierte enantioselektive Substitutionen von Allylchloriden mit Dialkylzinkverbindungen, 10.1002/(sici)1521-3757(19990201)111:3<391::aid-ange391>3.0.co;2-m
  30. Dübner Frank, Knochel Paul, Highly enantioselective copper-catalyzed substitution of allylic chlorides with diorganozincs, 10.1016/s0040-4039(00)01671-3
  31. Luchaco-Cullis Courtney A., Mizutani Hirotake, Murphy Kerry E., Hoveyda Amir H., Modular Pyridinyl Peptide Ligands in Asymmetric Catalysis: Enantioselective Synthesis of Quaternary Carbon Atoms Through Copper-Catalyzed Allylic Substitutions, 10.1002/1521-3757(20010417)113:8<1504::aid-ange1504>3.0.co;2-v
  32. Ohmiya Hirohisa, Yokobori Umi, Makida Yusuke, Sawamura Masaya, Copper-Catalyzed γ-Selective Allyl−Alkyl Coupling between Allylic Phosphates and Alkylboranes, 10.1021/ja9109105
  33. Nagao Kazunori, Yokobori Umi, Makida Yusuke, Ohmiya Hirohisa, Sawamura Masaya, Reversible 1,3-anti/syn-Stereochemical Courses in Copper-Catalyzed γ-Selective Allyl–Alkyl Coupling between Chiral Allylic Phosphates and Alkylboranes, 10.1021/ja302520h
  34. Shido Yoshinori, Yoshida Mika, Tanabe Masahito, Ohmiya Hirohisa, Sawamura Masaya, Copper-Catalyzed Enantioselective Allylic Substitution with Alkylboranes, 10.1021/ja3093955
  35. Delvos Lukas B., Vyas Devendra J., Oestreich Martin, Asymmetrische Synthese α-chiraler Allylsilane durch enantiokonvergente γ-selektive Kupfer(I)-katalysierte allylische Silylierung, 10.1002/ange.201300648
  36. Takeda Momotaro, Shintani Ryo, Hayashi Tamio, Enantioselective Synthesis of α-Tri- and α-Tetrasubstituted Allylsilanes by Copper-Catalyzed Asymmetric Allylic Substitution of Allyl Phosphates with Silylboronates, 10.1021/jo400888b
  37. Hazra Chinmoy K., Irran Elisabeth, Oestreich Martin, Regio- and Diastereoselective Copper(I)-Catalyzed Allylic Substitution of δ-Hydroxy Allylic Chlorides by a Silicon Nucleophile : Diastereoselective Allylic Substitution with a Silicon Nucleophile, 10.1002/ejoc.201300493
  38. Lee Yunmi, Akiyama Katsuhiro, Gillingham Dennis G., Brown M. Kevin, Hoveyda Amir H., Highly Site- and Enantioselective Cu-Catalyzed Allylic Alkylation Reactions with Easily Accessible Vinylaluminum Reagents, 10.1021/ja0782192
  39. Gao Fang, Hoveyda Amir H., α-Selective Ni-Catalyzed Hydroalumination of Aryl- and Alkyl-Substituted Terminal Alkynes: Practical Syntheses of Internal Vinyl Aluminums, Halides, or Boronates, 10.1021/ja104896b
  40. Akiyama Katsuhiro, Gao Fang, Hoveyda Amir H., Stereoisomerically Pure Trisubstituted Vinylaluminum Reagents and their Utility in Copper-Catalyzed Enantioselective Synthesis of 1,4-Dienes Containing Z or E Alkenes, 10.1002/ange.200905223
  41. Gao Fang, Carr James L., Hoveyda Amir H., Copper-Catalyzed Enantioselective Allylic Substitution with Readily Accessible Carbonyl- and Acetal-Containing Vinylboron Reagents, 10.1002/ange.201202856
  42. GERTH KLAUS, WASHAUSEN PETER, HÖFLE GERHARD, IRSCHIK HERBERT, REICHENBACH HANS, The Jerangolids: A Family of New Antifungal Compounds from Sorangium cellulosum (Myxobacteria). Production, Physico-chemical and Biological Properties of Jerangolid A., 10.7164/antibiotics.49.71
  43. Malloy Karla L., Suyama Takashi L., Engene Niclas, Debonsi Hosana, Cao Zhengyu, Matainaho Teatulohi, Spadafora Carmenza, Murray Thomas F., Gerwick William H., Credneramides A and B: Neuromodulatory Phenethylamine and Isopentylamine Derivatives of a Vinyl Chloride-Containing Fatty Acid from cf.Trichodesmiumsp. nov., 10.1021/np200611f
  44. Kobayashi Jun'ichi, Ishibashi Masami, Nakamura Hideshi, Ohizumi Yasushi, Yamasu Terufumi, Sasaki Takuma, Hirata Yoshimasa, Amphidinolide-A, a novel antineoplastic macrolide from the marine dinoflagellate Amphidinium sp., 10.1016/s0040-4039(00)85318-6
  45. Trost Barry M., Ball Zachary T., Jöge Thomas, A Chemoselective Reduction of Alkynes to (E)-Alkenes, 10.1021/ja026457l