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Versatile CuI/Pd0 dual catalysis for the synthesis of quaternary α-allylated carbonyl compounds: Development, mechanistic investigations and scope

Bibliographic reference Nahra, Fady ; Mace, Yohan ; Boreux, Arnaud ; Billard, François ; Riant, Olivier. Versatile CuI/Pd0 dual catalysis for the synthesis of quaternary α-allylated carbonyl compounds: Development, mechanistic investigations and scope. In: Chemistry: A European Journal, Vol. 20, no.35, p. 10970-10981 (2014)
Permanent URL http://hdl.handle.net/2078.1/155751
  1. Nahra Fady, Macé Yohan, Lambin Dominique, Riant Olivier, Copper/Palladium-Catalyzed 1,4 Reduction and Asymmetric Allylic Alkylation of α,β-Unsaturated Ketones: Enantioselective Dual Catalysis, 10.1002/anie.201208612
  2. Nahra Fady, Macé Yohan, Lambin Dominique, Riant Olivier, Copper/Palladium-Catalyzed 1,4 Reduction and Asymmetric Allylic Alkylation of α,β-Unsaturated Ketones: Enantioselective Dual Catalysis, 10.1002/ange.201208612
  3. Sawamura Masaya, Sudoh Masaki, Ito Yoshihiko, An Enantioselective Two-Component Catalyst System:  Rh−Pd-Catalyzed Allylic Alkylation of Activated Nitriles, 10.1021/ja954223e
  4. Trost Barry M., Luan Xinjun, Contemporaneous Dual Catalysis by Coupling Highly Transient Nucleophilic and Electrophilic Intermediates Generated in Situ, 10.1021/ja110501v
  5. Trost Barry M., Luan Xinjun, Miller Yan, Contemporaneous Dual Catalysis: Chemoselective Cross-Coupling of Catalytic Vanadium–Allenoate and π-Allylpalladium Intermediates, 10.1021/ja204817y
  6. Panteleev Jane, Zhang Lei, Lautens Mark, Domino Rhodium-Catalyzed Alkyne Arylation/Palladium-Catalyzed N Arylation: A Mechanistic Investigation, 10.1002/anie.201103692
  7. Panteleev Jane, Zhang Lei, Lautens Mark, Domino Rhodium-Catalyzed Alkyne Arylation/Palladium-Catalyzed N Arylation: A Mechanistic Investigation, 10.1002/ange.201103692
  8. 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
  9. Gu Zhenhua, Herrmann Aaron T., Zakarian Armen, Dual Ti-Ru Catalysis in the Direct Radical Haloalkylation of N-Acyl Oxazolidinones, 10.1002/anie.201101364
  10. Gu Zhenhua, Herrmann Aaron T., Zakarian Armen, Dual Ti-Ru Catalysis in the Direct Radical Haloalkylation of N-Acyl Oxazolidinones, 10.1002/ange.201101364
  11. 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
  12. Skucas Eduardas, MacMillan David W. C., Enantioselective α-Vinylation of Aldehydes via the Synergistic Combination of Copper and Amine Catalysis, 10.1021/ja303116v
  13. Friedman Adam A., Panteleev Jane, Tsoung Jennifer, Huynh Vaizanne, Lautens Mark, Rh/Pd Catalysis with Chiral and Achiral Ligands: Domino Synthesis of Aza-Dihydrodibenzoxepines, 10.1002/anie.201303659
  14. Friedman Adam A., Panteleev Jane, Tsoung Jennifer, Huynh Vaizanne, Lautens Mark, Rh/Pd Catalysis with Chiral and Achiral Ligands: Domino Synthesis of Aza-Dihydrodibenzoxepines, 10.1002/ange.201303659
  15. Vercruysse Sébastien, Cornelissen Loïc, Nahra Fady, Collard Laurent, Riant Olivier, CuI/Pd0Cooperative Dual Catalysis: Tunable Stereoselective Construction of Tetra-Substituted Alkenes, 10.1002/chem.201304284
  16. Vaxelaire Carine, Winter Philipp, Christmann Mathias, Eintopfreaktionen beschleunigen die Synthese pharmazeutischer Wirkstoffe, 10.1002/ange.201100059
  17. Vaxelaire Carine, Winter Philipp, Christmann Mathias, One-Pot Reactions Accelerate the Synthesis of Active Pharmaceutical Ingredients, 10.1002/anie.201100059
  18. Allen Anna E., MacMillan David W. C., Synergistic catalysis: A powerful synthetic strategy for new reaction development, 10.1039/c2sc00907b
  19. Patil Nitin T., Shinde Valmik S., Gajula Balakrishna, A one-pot catalysis: the strategic classification with some recent examples, 10.1039/c1ob06432k
  20. Lee Ji Min, Na Youngim, Han Hoon, Chang Sukbok, Cooperative multi-catalyst systems for one-pot organic transformations, 10.1039/b309033g
  21. Wende Raffael C., Schreiner Peter R., Evolution of asymmetric organocatalysis: multi- and retrocatalysis, 10.1039/c2gc35160a
  22. 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
  23. Shao Zhihui, Zhang Hongbin, Combining transition metal catalysis and organocatalysis: a broad new concept for catalysis, 10.1039/b901258n
  24. Rueping Magnus, Koenigs Rene M., Atodiresei Iuliana, Unifying Metal and Brønsted Acid Catalysis-Concepts, Mechanisms, and Classifications, 10.1002/chem.201001140
  25. 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
  26. Chai Zhuo, Rainey Trevor J., Pd(II)/Brønsted Acid Catalyzed Enantioselective Allylic C–H Activation for the Synthesis of Spirocyclic Rings, 10.1021/ja2102407
  27. 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
  28. Pàmies Oscar, Bäckvall Jan-E., Combination of Enzymes and Metal Catalysts. A Powerful Approach in Asymmetric Catalysis, 10.1021/cr020029g
  29. Zhong Cheng, Shi Xiaodong, When Organocatalysis Meets Transition-Metal Catalysis, 10.1002/ejoc.201000004
  30. Lee Jin Hee, Han Kiwon, Kim Mahn-Joo, Park Jaiwook, Chemoenzymatic Dynamic Kinetic Resolution of Alcohols and Amines, 10.1002/ejoc.200900935
  31. Conley Brian L., Pennington-Boggio Megan K., Boz Emine, Williams Travis J., Discovery, Applications, and Catalytic Mechanisms of Shvo’s Catalyst, 10.1021/cr9003133
  32. 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
  33. Cossy Janine, Bargiggia Frédéric, BouzBouz Samir, Tandem Cross-Metathesis/Hydrogenation/Cyclization Reactions by Using Compatible Catalysts, 10.1021/ol027347m
  34. 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
  35. Goldman A. S., Catalytic Alkane Metathesis by Tandem Alkane Dehydrogenation-Olefin Metathesis, 10.1126/science.1123787
  36. 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
  37. 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
  38. 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
  39. 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
  40. Park Jongwoo, Hong Sukwon, Cooperative bimetallic catalysis in asymmetric transformations, 10.1039/c2cs35129c
  41. 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
  42. Weaver Jimmie D., Recio Antonio, Grenning Alexander J., Tunge Jon A., Transition Metal-Catalyzed Decarboxylative Allylation and Benzylation Reactions, 10.1021/cr1002744
  43. Trost Barry M., Xu Jiayi, Schmidt Thomas, Palladium-Catalyzed Decarboxylative Asymmetric Allylic Alkylation of Enol Carbonates, 10.1021/ja9053948
  44. 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
  45. 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
  46. 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
  47. Bélanger Étienne, Cantin Katy, Messe Olivier, Tremblay Mélanie, Paquin Jean-François, Enantioselective Pd-Catalyzed Allylation Reaction of Fluorinated Silyl Enol Ethers, 10.1021/ja067501q
  48. Behenna Douglas C., Stoltz Brian M., The Enantioselective Tsuji Allylation, 10.1021/ja044812x
  49. D. C. Behenna B. M. Stoltz J. T. Mohr A. M. Harned 2006
  50. 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
  51. 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
  52. Mukherjee Herschel, McDougal Nolan T., Virgil Scott C., Stoltz Brian M., A Catalytic, Asymmetric Formal Synthesis of (+)-Hamigeran B, 10.1021/ol102669z
  53. 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
  54. 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
  55. 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
  56. 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
  57. ee
  58. van der Baan J.L, Bickelhaupt F, Palladium(II)-catalyzed claisen rearrangement of allyl vinyl ethers, 10.1016/s0040-4039(00)85449-0
  59. Kimura Masanari, Kiyama Iku, Tomizawa Tatsuya, Horino Yoshikazu, Tanaka Shuji, Tamaru Yoshinao, Allylation of aldehydes via Umpolung of π-allylpalladium(II) with triethylborane, 10.1016/s0040-4039(99)01359-3
  60. von Matt Peter, Pfaltz Andreas, Chiral Phosphinoaryldihydrooxazoles as Ligands in Asymmetric Catalysis: Pd-Catalyzed Allylic Substitution, 10.1002/anie.199305661
  61. Von Matt Peter, Pfaltz Andreas, Chirale Phosphinoaryldihydrooxazole als Liganden in der asymmetrischen Katalyse: Pd-katalysierte allylische Substitution, 10.1002/ange.19931050430
  62. Tani Kousuke, Behenna Douglas C., McFadden Ryan M., Stoltz Brian M., A Facile and Modular Synthesis of Phosphinooxazoline Ligands, 10.1021/ol070884s
  63. Heller Douglas P., Goldberg Daniel R., Wulff William D., Positive Cooperativity of Product Mimics in the Asymmetric Autoinduction of Diels−Alder Reactions Catalyzed by a VAPOL−Aluminum Catalyst, 10.1021/ja971246f
  64. 2 Ph.D Thesis 2010
  65. Nicolaou K. C., Hale Christopher R. H., Nilewski Christian, A Total Synthesis Trilogy: Calicheamicin γ1I, Taxol®, and Brevetoxin A, 10.1002/tcr.201200005
  66. Kleinke Andrew S., Webb Damien, Jamison Timothy F., Recent progress in the synthesis of oxepanes and medium ring ethers, 10.1016/j.tet.2012.05.081
  67. Mak S. Y. Frankie, Curtis Neil R., Payne Andrew N., Congreve Miles S., Wildsmith Andrew J., Francis Craig L., Davies John E., Pascu Sofia I., Burton Jonathan W., Holmes Andrew B., Synthesis of (+)-Obtusenyne, 10.1002/chem.200701567
  68. Molander Gary A., St. Jean David J., Haas Julia, Toward a General Route to the Eunicellin Diterpenes:  The Asymmetric Total Synthesis of Deacetoxyalcyonin Acetate, 10.1021/ja0398464