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Copper/palladium-catalyzed 1,4 reduction and asymmetric allylic alkylation of α,β-unsaturated ketones: Enantioselective dual catalysis

Bibliographic reference Nahra, Fady ; Macé, Y. ; Lambin, D. ; Riant, Olivier. Copper/palladium-catalyzed 1,4 reduction and asymmetric allylic alkylation of α,β-unsaturated ketones: Enantioselective dual catalysis . In: Angewandte Chemie - International Edition, Vol. 52, no.11, p. 3208-3212 (2013)
Permanent URL http://hdl.handle.net/2078.1/127480
  1. Lee Ji Min, Na Youngim, Han Hoon, Chang Sukbok, Cooperative multi-catalyst systems for one-pot organic transformations, 10.1039/b309033g
  2. Wasilke Julia-Christina, Obrey Stephen J., Baker R. Tom, Bazan Guillermo C., Concurrent Tandem Catalysis, 10.1021/cr020018n
  3. Bruggink Alle, Schoevaart Rob, Kieboom Tom, Concepts of Nature in Organic Synthesis:  Cascade Catalysis and Multistep Conversions in Concert, 10.1021/op0340311
  4. Ambrosini Lisa M., Lambert Tristan H., Multicatalysis: Advancing Synthetic Efficiency and Inspiring Discovery, 10.1002/cctc.200900323
  5. Ramachary Dhevalapally B., Jain Sangeeta, Sequential one-pot combination of multi-component and multi-catalysis cascade reactions: an emerging technology in organic synthesis, 10.1039/c0ob00611d
  6. Kamijo, Multimetallic Catalysis in Organic Synthesis, 1 (2004)
  7. Pérez-Temprano Mónica H., Casares Juan A., Espinet Pablo, Bimetallic Catalysis using Transition and Group 11 Metals: An Emerging Tool for CC Coupling and Other Reactions, 10.1002/chem.201102888
  8. Hirner Joshua J., Shi Yili, Blum Suzanne A., Organogold Reactivity with Palladium, Nickel, and Rhodium: Transmetalation, Cross-Coupling, and Dual Catalysis, 10.1021/ar200055y
  9. Park Young Jun, Park Jung-Woo, Jun Chul-Ho, Metal−Organic Cooperative Catalysis in C−H and C−C Bond Activation and Its Concurrent Recovery, 10.1021/ar700133y
  10. Shao Zhihui, Zhang Hongbin, Combining transition metal catalysis and organocatalysis: a broad new concept for catalysis, 10.1039/b901258n
  11. Rueping Magnus, Koenigs Rene M., Atodiresei Iuliana, Unifying Metal and Brønsted Acid Catalysis-Concepts, Mechanisms, and Classifications, 10.1002/chem.201001140
  12. DiRocco Daniel A., Rovis Tomislav, Catalytic Asymmetric α-Acylation of Tertiary Amines Mediated by a Dual Catalysis Mode: N-Heterocyclic Carbene and Photoredox Catalysis, 10.1021/ja3030164
  13. Chai Zhuo, Rainey Trevor J., Pd(II)/Brønsted Acid Catalyzed Enantioselective Allylic C–H Activation for the Synthesis of Spirocyclic Rings, 10.1021/ja2102407
  14. Ye Yingda, Sanford Melanie S., Merging Visible-Light Photocatalysis and Transition-Metal Catalysis in the Copper-Catalyzed Trifluoromethylation of Boronic Acids with CF3I, 10.1021/ja301553c
  15. Pàmies Oscar, Bäckvall Jan-E., Combination of Enzymes and Metal Catalysts. A Powerful Approach in Asymmetric Catalysis, 10.1021/cr020029g
  16. Zhong Cheng, Shi Xiaodong, When Organocatalysis Meets Transition-Metal Catalysis, 10.1002/ejoc.201000004
  17. Lee Jin Hee, Han Kiwon, Kim Mahn-Joo, Park Jaiwook, Chemoenzymatic Dynamic Kinetic Resolution of Alcohols and Amines, 10.1002/ejoc.200900935
  18. Conley Brian L., Pennington-Boggio Megan K., Boz Emine, Williams Travis J., Discovery, Applications, and Catalytic Mechanisms of Shvo’s Catalyst, 10.1021/cr9003133
  19. Marr Andrew C., Liu Shifang, Combining bio- and chemo-catalysis: from enzymes to cells, from petroleum to biomass, 10.1016/j.tibtech.2011.01.005
  20. Cossy Janine, Bargiggia Frédéric, BouzBouz Samir, Tandem Cross-Metathesis/Hydrogenation/Cyclization Reactions by Using Compatible Catalysts, 10.1021/ol027347m
  21. Nishibayashi Yoshiaki, Yoshikawa Masato, Inada Youichi, Hidai Masanobu, Uemura Sakae, Ruthenium- and Platinum-Catalyzed Sequential Reactions:  Selective Synthesis of Fused Polycyclic Compounds from Propargylic Alcohols and Alkenes, 10.1021/ja045532k
  22. Goldman A. S., Catalytic Alkane Metathesis by Tandem Alkane Dehydrogenation-Olefin Metathesis, 10.1126/science.1123787
  23. Cernak Tim A., Lambert Tristan H., Multicatalytic Synthesis of α-Pyrrolidinyl Ketones via a Tandem Palladium(II)/Indium(III)-Catalyzed Aminochlorocarbonylation/Friedel−Crafts Acylation Reaction, 10.1021/ja809897f
  24. Takahashi Kohei, Yamashita Makoto, Ichihara Takeo, Nakano Koji, Nozaki Kyoko, High-Yielding Tandem Hydroformylation/Hydrogenation of a Terminal Olefin to Produce a Linear Alcohol Using a Rh/Ru Dual Catalyst System, 10.1002/anie.201001327
  25. Takahashi Kohei, Yamashita Makoto, Ichihara Takeo, Nakano Koji, Nozaki Kyoko, High-Yielding Tandem Hydroformylation/Hydrogenation of a Terminal Olefin to Produce a Linear Alcohol Using a Rh/Ru Dual Catalyst System, 10.1002/ange.201001327
  26. Kuriyama Masami, Takeichi Tsubasa, Ito Masaaki, Yamasaki Noritsugu, Yamamura Ryota, Demizu Yosuke, Onomura Osamu, Monoallylation of 1,2-Diols by Pd/Sn Bimetallic Catalysis, 10.1002/chem.201102709
  27. Motoyama Kazuki, Ikeda Masahiro, Miyake Yoshihiro, Nishibayashi Yoshiaki, Ruthenium- and Copper-Catalyzed Enantioselective Propargylic Alkylation of Propargylic Alcohols with β-Keto Phosphonates, 10.1021/om300219f
  28. Skucas Eduardas, MacMillan David W. C., Enantioselective α-Vinylation of Aldehydes via the Synergistic Combination of Copper and Amine Catalysis, 10.1021/ja303116v
  29. Park Jongwoo, Hong Sukwon, Cooperative bimetallic catalysis in asymmetric transformations, 10.1039/c2cs35129c
  30. Sawamura Masaya, Sudoh Masaki, Ito Yoshihiko, An Enantioselective Two-Component Catalyst System:  Rh−Pd-Catalyzed Allylic Alkylation of Activated Nitriles, 10.1021/ja954223e
  31. Trost Barry M., Luan Xinjun, Contemporaneous Dual Catalysis by Coupling Highly Transient Nucleophilic and Electrophilic Intermediates Generated in Situ, 10.1021/ja110501v
  32. Trost Barry M., Luan Xinjun, Miller Yan, Contemporaneous Dual Catalysis: Chemoselective Cross-Coupling of Catalytic Vanadium–Allenoate and π-Allylpalladium Intermediates, 10.1021/ja204817y
  33. Panteleev Jane, Zhang Lei, Lautens Mark, Domino Rhodium-Catalyzed Alkyne Arylation/Palladium-Catalyzed N Arylation: A Mechanistic Investigation, 10.1002/anie.201103692
  34. Panteleev Jane, Zhang Lei, Lautens Mark, Domino Rhodium-Catalyzed Alkyne Arylation/Palladium-Catalyzed N Arylation: A Mechanistic Investigation, 10.1002/ange.201103692
  35. Shirakawa Eiji, Ikeda Daiji, Masui Seiji, Yoshida Masatoshi, Hayashi Tamio, Iron–Copper Cooperative Catalysis in the Reactions of Alkyl Grignard Reagents: Exchange Reaction with Alkenes and Carbometalation of Alkynes, 10.1021/ja206745w
  36. Gu Zhenhua, Herrmann Aaron T., Zakarian Armen, Dual Ti-Ru Catalysis in the Direct Radical Haloalkylation of N-Acyl Oxazolidinones, 10.1002/anie.201101364
  37. Gu Zhenhua, Herrmann Aaron T., Zakarian Armen, Dual Ti-Ru Catalysis in the Direct Radical Haloalkylation of N-Acyl Oxazolidinones, 10.1002/ange.201101364
  38. Keith John���A., Henry Patrick���M., Zum Mechanismus der Wacker-Reaktion: zwei Hydroxypalladierungen!, 10.1002/ange.200902194
  39. Keith John���A., Henry Patrick���M., The Mechanism of the Wacker Reaction: A Tale of Two Hydroxypalladations, 10.1002/anie.200902194
  40. Sonogashira, Metal-Catalyzed Reactions, 203 (1998)
  41. Nicolaou K. C., Bulger Paul G., Sarlah David, Palladium-Catalyzed Cross-Coupling Reactions in Total Synthesis, 10.1002/anie.200500368
  42. Nicolaou K. C., Bulger Paul G., Sarlah David, Palladiumkatalysierte Kreuzkupplungen in der Totalsynthese, 10.1002/ange.200500368
  43. Chinchilla Rafael, Nájera Carmen, The Sonogashira Reaction:  A Booming Methodology in Synthetic Organic Chemistry†, 10.1021/cr050992x
  44. Doucet Henri, Hierso Jean-Cyrille, Palladium-Based Catalytic Systems for the Synthesis of Conjugated Enynes by Sonogashira Reactions and Related Alkynylations, 10.1002/anie.200602761
  45. Doucet Henri, Hierso Jean-Cyrille, Palladium-Katalysatorsysteme für die Synthese von konjugierten Eninen durch Sonogashira-Kupplungen und verwandte Alkinylierungen, 10.1002/ange.200602761
  46. Deschamp Julia, Hermant Thomas, Riant Olivier, An easy route toward enantio-enriched polycyclic derivatives via an asymmetric domino conjugate reduction–aldol cyclization catalyzed by a chiral Cu(I) complex, 10.1016/j.tet.2011.07.039
  47. Welle Alexandre, Cirriez Virginie, Riant Olivier, Copper catalyzed tandem conjugated borylation–aldol reaction, 10.1016/j.tet.2011.07.062
  48. Welle Alexandre, Petrignet Julien, Tinant Bernard, Wouters Johan, Riant Olivier, Copper-Catalysed Domino Silylative Aldol Reaction Leading to Stereocontrolled Chiral Quaternary Carbons, 10.1002/chem.201000907
  49. Deschamp Julia, Riant Olivier, Efficient Construction of Polycyclic Derivatives via a Highly Selective CuI-Catalyzed Domino Reductive-Aldol Cyclization, 10.1021/ol802879f
  50. Deschamp Julia, Chuzel Olivier, Hannedouche Jérôme, Riant Olivier, Highly Diastereo- and Enantioselective Copper-Catalyzed Domino Reduction/Aldol Reaction of Ketones with Methyl Acrylate, 10.1002/anie.200503791
  51. Deschamp Julia, Chuzel Olivier, Hannedouche Jérôme, Riant Olivier, Highly Diastereo- and Enantioselective Copper-Catalyzed Domino Reduction/Aldol Reaction of Ketones with Methyl Acrylate, 10.1002/ange.200503791
  52. Chuzel Olivier, Deschamp Julia, Chausteur Christophe, Riant Olivier, Copper(I)-Catalyzed Enantio- and Diastereoselective Tandem Reductive Aldol Reaction, 10.1021/ol062398v
  53. Welle Alexandre, Díez-González Silvia, Tinant Bernard, Nolan Steven P., Riant Olivier, A Three-Component Tandem Reductive Aldol Reaction Catalyzed by N-Heterocyclic Carbene−Copper Complexes, 10.1021/ol062495o
  54. Trost Barry M., Schroeder Gretchen M., Palladium-Catalyzed Asymmetric Allylic Alkylation of Ketone Enolates, 10.1002/chem.200400666
  55. Trost Barry M., Pd Asymmetric Allylic Alkylation (AAA). A Powerful Synthetic Tool, 10.1248/cpb.50.1
  56. Trost Barry M., Van Vranken David L., Asymmetric Transition Metal-Catalyzed Allylic Alkylations, 10.1021/cr9409804
  57. Trost Barry M., Designing a Receptor for Molecular Recognition in a Catalytic Synthetic Reaction:  Allylic Alkylation, 10.1021/ar9501129
  58. Behenna Douglas C., Liu Yiyang, Yurino Taiga, Kim Jimin, White David E., Virgil Scott C., Stoltz Brian M., Enantioselective construction of quaternary N-heterocycles by palladium-catalysed decarboxylative allylic alkylation of lactams, 10.1038/nchem.1222
  59. Zhao Xiaohu, Liu Delong, Guo Hui, Liu Yangang, Zhang Wanbin, C–N Bond Cleavage of Allylic Amines via Hydrogen Bond Activation with Alcohol Solvents in Pd-Catalyzed Allylic Alkylation of Carbonyl Compounds, 10.1021/ja209373k
  60. Weaver Jimmie D., Recio Antonio, Grenning Alexander J., Tunge Jon A., Transition Metal-Catalyzed Decarboxylative Allylation and Benzylation Reactions, 10.1021/cr1002744
  61. Trost Barry M., Xu Jiayi, Schmidt Thomas, Palladium-Catalyzed Decarboxylative Asymmetric Allylic Alkylation of Enol Carbonates, 10.1021/ja9053948
  62. Trost Barry M., Schäffner Benjamin, Osipov Maksim, Wilton Donna A. A., Palladium-Catalyzed Decarboxylative Asymmetric Allylic Alkylation of β-ketoesters: An Unusual Counterion Effect, 10.1002/anie.201007803
  63. Trost Barry M., Schäffner Benjamin, Osipov Maksim, Wilton Donna A. A., Palladium-Catalyzed Decarboxylative Asymmetric Allylic Alkylation of β-ketoesters: An Unusual Counterion Effect, 10.1002/ange.201007803
  64. Doyle Abigail G., Jacobsen Eric N., Enantioselective Alkylations of Tributyltin Enolates Catalyzed by Cr(salen)Cl:  Access to Enantiomerically Enriched All-Carbon Quaternary Centers, 10.1021/ja043601p
  65. Bélanger Étienne, Cantin Katy, Messe Olivier, Tremblay Mélanie, Paquin Jean-François, Enantioselective Pd-Catalyzed Allylation Reaction of Fluorinated Silyl Enol Ethers, 10.1021/ja067501q
  66. Behenna Douglas C., Stoltz Brian M., The Enantioselective Tsuji Allylation, 10.1021/ja044812x
  67. D. C. Behenna B. M. Stoltz J. T. Mohr A. M. Harned 2006
  68. Hong Allen Y., Krout Michael R., Jensen Thomas, Bennett Nathan B., Harned Andrew M., Stoltz Brian M., Ring-Contraction Strategy for the Practical, Scalable, Catalytic Asymmetric Synthesis of Versatile γ-Quaternary Acylcyclopentenes, 10.1002/anie.201007814
  69. Hong Allen Y., Krout Michael R., Jensen Thomas, Bennett Nathan B., Harned Andrew M., Stoltz Brian M., Ring-Contraction Strategy for the Practical, Scalable, Catalytic Asymmetric Synthesis of Versatile γ-Quaternary Acylcyclopentenes, 10.1002/ange.201007814
  70. Mukherjee Herschel, McDougal Nolan T., Virgil Scott C., Stoltz Brian M., A Catalytic, Asymmetric Formal Synthesis of (+)-Hamigeran B, 10.1021/ol102669z
  71. Bennett Nathan B., Hong Allen Y., Harned Andrew M., Stoltz Brian M., Synthesis of enantioenriched γ-quaternary cycloheptenones using a combined allylic alkylation/Stork–Danheiser approach: preparation of mono-, bi-, and tricyclic systems, 10.1039/c1ob06189e
  72. Behenna Douglas C., Mohr Justin T., Sherden Nathaniel H., Marinescu Smaranda C., Harned Andrew M., Tani Kousuke, Seto Masaki, Ma Sandy, Novák Zoltán, Krout Michael R., McFadden Ryan M., Roizen Jennifer L., Enquist John A., White David E., Levine Samantha R., Petrova Krastina V., Iwashita Akihiko, Virgil Scott C., Stoltz Brian M., Enantioselective Decarboxylative Alkylation Reactions: Catalyst Development, Substrate Scope, and Mechanistic Studies, 10.1002/chem.201003383
  73. Tsuji Jiro, Minami Ichiro, Shimizu Isao, PALLADIUM-CATALYZED ALLYLATION OF KETONES AND ALDEHYDES WITH ALLYLIC CARBONATES VIA SILYL ENOL ETHERS UNDER NEUTRAL CONDITIONS, 10.1246/cl.1983.1325
  74. Tsuji Jiro, Minami Ichiro, Shimizu Isao, Kataoka Hideaki, ENONE FORMATION FROM ALLYL β-KETO ESTERS, ALKENYL ALLYL CARBONATES, SILYL ENOL ETHERS, AND ENOL ACETATES BY THE PHOSPHINE-FREE PALLADIUM CATALYST, 10.1246/cl.1984.1133
  75. Shimizu Masaki, Construction of Asymmetric Quaternary Carbon Centers with High Enantioselectivity, 10.1002/anie.201101720
  76. Shimizu Masaki, Aufbau von asymmetrischen quartären Kohlenstoffzentren mit hoher Enantioselektivität, 10.1002/ange.201101720
  77. Wang Baomin, Tu Yong Qiang, Stereoselective Construction of Quaternary Carbon Stereocenters via a Semipinacol Rearrangement Strategy, 10.1021/ar200082p
  78. Quaternary Stereocenters : Challenges and Solutions for Organic Synthesis, ISBN:9783527606856, 10.1002/3527606858
  79. Mankad Neal P., Laitar David S., Sadighi Joseph P., Synthesis, Structure, and Alkyne Reactivity of a Dimeric (Carbene)copper(I) Hydride, 10.1021/om0496380
  80. van der Baan J.L, Bickelhaupt F, Palladium(II)-catalyzed claisen rearrangement of allyl vinyl ethers, 10.1016/s0040-4039(00)85449-0
  81. 2 3 S
  82. von Matt Peter, Pfaltz Andreas, Chiral Phosphinoaryldihydrooxazoles as Ligands in Asymmetric Catalysis: Pd-Catalyzed Allylic Substitution, 10.1002/anie.199305661
  83. Von Matt Peter, Pfaltz Andreas, Chirale Phosphinoaryldihydrooxazole als Liganden in der asymmetrischen Katalyse: Pd-katalysierte allylische Substitution, 10.1002/ange.19931050430
  84. Tani Kousuke, Behenna Douglas C., McFadden Ryan M., Stoltz Brian M., A Facile and Modular Synthesis of Phosphinooxazoline Ligands, 10.1021/ol070884s
  85. t