User menu

CuI/Pd0 cooperative dual catalysis: Tunable stereoselective construction of tetra-substituted alkenes

Bibliographic reference Vercruysse, Sébastien ; Cornelissen, Loïc ; Nahra, Fady ; Collard, Laurent ; Riant, Olivier. CuI/Pd0 cooperative dual catalysis: Tunable stereoselective construction of tetra-substituted alkenes. In: Chemistry: A European Journal, Vol. 20, no. 7, p. 1834-1838 (2014)
Permanent URL http://hdl.handle.net/2078.1/155767
  1. Allen Anna E., MacMillan David W. C., Synergistic catalysis: A powerful synthetic strategy for new reaction development, 10.1039/c2sc00907b
  2. 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
  3. 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
  4. Skucas Eduardas, MacMillan David W. C., Enantioselective α-Vinylation of Aldehydes via the Synergistic Combination of Copper and Amine Catalysis, 10.1021/ja303116v
  5. 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
  6. Gu Zhenhua, Herrmann Aaron T., Zakarian Armen, Dual Ti-Ru Catalysis in the Direct Radical Haloalkylation of N-Acyl Oxazolidinones, 10.1002/anie.201101364
  7. Gu Zhenhua, Herrmann Aaron T., Zakarian Armen, Dual Ti-Ru Catalysis in the Direct Radical Haloalkylation of N-Acyl Oxazolidinones, 10.1002/ange.201101364
  8. Patil Nitin T., Shinde Valmik S., Gajula Balakrishna, A one-pot catalysis: the strategic classification with some recent examples, 10.1039/c1ob06432k
  9. Lee Ji Min, Na Youngim, Han Hoon, Chang Sukbok, Cooperative multi-catalyst systems for one-pot organic transformations, 10.1039/b309033g
  10. Wende Raffael C., Schreiner Peter R., Evolution of asymmetric organocatalysis: multi- and retrocatalysis, 10.1039/c2gc35160a
  11. Sawamura Masaya, Sudoh Masaki, Ito Yoshihiko, An Enantioselective Two-Component Catalyst System:  Rh−Pd-Catalyzed Allylic Alkylation of Activated Nitriles, 10.1021/ja954223e
  12. Trost Barry M., Luan Xinjun, Contemporaneous Dual Catalysis by Coupling Highly Transient Nucleophilic and Electrophilic Intermediates Generated in Situ, 10.1021/ja110501v
  13. Trost Barry M., Luan Xinjun, Miller Yan, Contemporaneous Dual Catalysis: Chemoselective Cross-Coupling of Catalytic Vanadium–Allenoate and π-Allylpalladium Intermediates, 10.1021/ja204817y
  14. Panteleev Jane, Zhang Lei, Lautens Mark, Domino Rhodium-Catalyzed Alkyne Arylation/Palladium-Catalyzed N Arylation: A Mechanistic Investigation, 10.1002/anie.201103692
  15. Panteleev Jane, Zhang Lei, Lautens Mark, Domino Rhodium-Catalyzed Alkyne Arylation/Palladium-Catalyzed N Arylation: A Mechanistic Investigation, 10.1002/ange.201103692
  16. 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
  17. Negishi Ei-ichi, Huang Zhihong, Wang Guangwei, Mohan Swathi, Wang Chao, Hattori Hatsuhiko, Recent Advances in Efficient and Selective Synthesis of Di-, Tri-, and Tetrasubstituted Alkenes via Pd-Catalyzed Alkenylation−Carbonyl Olefination Synergy, 10.1021/ar800038e
  18. Knochel, Comprehensive Organic Synthesis-Selectivity, Strategy and Efficiency in Modern Organic Chemistry, 865 (1992)
  19. Flynn Alison B., Ogilvie William W., Stereocontrolled Synthesis of Tetrasubstituted Olefins, 10.1021/cr050051k
  20. Alonso Francisco, Beletskaya Irina P., Yus Miguel, Transition-Metal-Catalyzed Addition of Heteroatom−Hydrogen Bonds to Alkynes, 10.1021/cr0201068
  21. He Zhiheng, Kirchberg Sylvia, Fröhlich Roland, Studer Armido, Oxidative Heck Arylation for the Stereoselective Synthesis of Tetrasubstituted Olefins Using Nitroxides as Oxidants, 10.1002/anie.201108211
  22. He Zhiheng, Kirchberg Sylvia, Fröhlich Roland, Studer Armido, Oxidative Heck-Arylierung zur stereoselektiven Synthese von tetrasubstituierten Olefinen mit Nitroxiden als Oxidationsmittel, 10.1002/ange.201108211
  23. Itami Kenichiro, Kamei Toshiyuki, Yoshida Jun-ichi, Diversity-Oriented Synthesis of Tamoxifen-type Tetrasubstituted Olefins, 10.1021/ja037566i
  24. Das Jaya Prakash, Chechik Helena, Marek Ilan, A unique approach to aldol products for the creation of all-carbon quaternary stereocentres, 10.1038/nchem.131
  25. Dutta Bishnu, Gilboa Noga, Marek Ilan, Highly Diastereoselective Preparation of Homoallylic Alcohols Containing Two Contiguous Quaternary Stereocenters in Acyclic Systems from Simple Terminal Alkynes, 10.1021/ja101371x
  26. Basheer Ahmad, Marek Ilan, Recent advances in carbocupration of α-heterosubstituted alkynes, 10.3762/bjoc.6.77
  27. Finn M. G., Sharpless K. Barry, Mechanism of asymmetric epoxidation. 2. Catalyst structure, 10.1021/ja00001a019
  28. Normant J.F., Bourgain M., Synthese stereospecifique and reactivite d' organocuivreux vinyliques, 10.1016/s0040-4039(01)96925-4
  29. Normant Jean F., Alexakis Alexandre, Carbometallation (C-Metallation) of Alkynes: Stereospecific Synthesis of Alkenyl Derivatives, 10.1055/s-1981-29622
  30. Colvin, The Chemistry of Organic Silicon Compounds, 1667 (2003)
  31. Hiyama, Handbook of Organopalladium Chemistry for Organic Synthesis, 285 (2003)
  32. Denmark, Metal-Catalyzed Cross-Coupling Reactions, 163 (2008)
  33. Hartmann Eduard, Oestreich Martin, Asymmetric Conjugate Silyl Transfer in Iterative Catalytic Sequences: Synthesis of the C7-C16 Fragment of (+)-Neopeltolide, 10.1002/anie.201002916
  34. Hartmann Eduard, Oestreich Martin, Der asymmetrische konjugierte Silyltransfer in iterativen katalytischen Sequenzen: Synthese des C7-C16-Fragments von (+)-Neopeltolid, 10.1002/ange.201002916
  35. Balskus Emily P., Jacobsen Eric N., α,β-Unsaturated β-Silyl Imide Substrates for Catalytic, Enantioselective Conjugate Additions:  A Total Synthesis of (+)-Lactacystin and the Discovery of a New Proteasome Inhibitor, 10.1021/ja061970a
  36. Hartmann Eduard, Vyas Devendra J., Oestreich Martin, Enantioselective formal hydration of α,β-unsaturated acceptors: asymmetric conjugate addition of silicon and boron nucleophiles, 10.1039/c1cc10528k
  37. Walter Christian, Auer Gertrud, Oestreich Martin, Rhodium-Catalyzed Enantioselective Conjugate Silyl Transfer: 1,4-Addition of Silyl Boronic Esters to Cyclic Enones and Lactones, 10.1002/anie.200601747
  38. Walter Christian, Auer Gertrud, Oestreich Martin, Rhodiumkatalysierter enantioselektiver konjugierter Silyltransfer: 1,4-Addition von Silylboronsäureestern an cyclische Enone und Lactone, 10.1002/ange.200601747
  39. Walter Christian, Fröhlich Roland, Oestreich Martin, Rhodium(I)-catalyzed enantioselective 1,4-addition of nucleophilic silicon, 10.1016/j.tet.2009.01.111
  40. Calderone Joseph A., Santos Webster L., Copper(II)-Catalyzed Silyl Conjugate Addition to α,β-Unsaturated Conjugated Compounds: Brønsted Base-Assisted Activation of Si–B Bond in Water, 10.1021/ol300618j
  41. Lee Kang-sang, Hoveyda Amir H., Enantioselective Conjugate Silyl Additions to Cyclic and Acyclic Unsaturated Carbonyls Catalyzed by Cu Complexes of Chiral N-Heterocyclic Carbenes, 10.1021/ja910989n
  42. Walter Christian, Oestreich Martin, Catalytic Asymmetric CSi Bond Formation to Acyclic α,β-Unsaturated Acceptors by RhI-Catalyzed Conjugate Silyl Transfer Using a SiB Linkage, 10.1002/anie.200800361
  43. Walter Christian, Oestreich Martin, Katalytische asymmetrische C-Si-Bindungsknüpfung an acyclischen α,β-ungesättigten Akzeptoren durch RhI-katalysierten konjugierten Silyltransfer mithilfe einer Si-B-Bindung, 10.1002/ange.200800361
  44. Clark Christopher T., Lake Jason F., Scheidt Karl A., Copper(I)-Catalyzed Disilylation of Alkylidene Malonates Employing a Lewis Base Activation Strategy, 10.1021/ja038530t
  45. Ibrahem Ismail, Santoro Stefano, Himo Fahmi, Córdova Armando, Enantioselective Conjugate Silyl Additions to α,β-Unsaturated Aldehydes Catalyzed by Combination of Transition Metal and Chiral Amine Catalysts, 10.1002/adsc.201000908
  46. 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
  47. Oestreich Martin, Hartmann Eduard, Mewald Marius, Activation of the Si–B Interelement Bond: Mechanism, Catalysis, and Synthesis, 10.1021/cr3003517
  48. Auer Gertrud, Oestreich Martin, Silylzincation of carbon–carbon multiple bonds revisited, 10.1039/b513528a
  49. Weickgenannt Andreas, Oestreich Martin, Silicon- and Tin-Based Cuprates: Now Catalytic in Copper!, 10.1002/chem.200902222
  50. Suginome Michinori, Matsuda Takanori, Ito Yoshihiko, Convenient Preparation of Silylboranes, 10.1021/om000254t
  51. Suginome* Michinori, Ohmori Yutaka, Ito* Yoshihiko, Palladium-catalyzed regioselective silaboration of 1,2-dienes, 10.1016/s0022-328x(00)00472-1
  52. Hayami Hiroshi, Sato Mitsuyoshi, Kanemoto Shigekazu, Morizawa Yoshitomi, Oshima Koichiro, Nozaki Hitosi, Transition-metal-catalyzed silylmetalation of acetylenes and its application to the stereoselective synthesis of steroidal side chains, 10.1021/ja00351a069
  53. Wang Peng, Yeo Xue-Liang, Loh Teck-Peng, Copper-Catalyzed Highly Regioselective Silylcupration of Terminal Alkynes to Form α-Vinylsilanes, 10.1021/ja109464u
  54. Trost Barry M., Ball Zachary T., Addition of Metalloid Hydrides to Alkynes: Hydrometallation with Boron, Silicon, and Tin, 10.1055/s-2005-861874
  55. Brunner Henri, A New Hydrosilylation Mechanism—New Preparative Opportunities, 10.1002/anie.200301742
  56. Brunner Henri, Neuer Hydrosilylierungsmechanismus– neue präparative Möglichkeiten, 10.1002/ange.200301742
  57. Trost Barry M., Ball Zachary T., Markovnikov Alkyne Hydrosilylation Catalyzed by Ruthenium Complexes, 10.1021/ja0121033
  58. Na Youngim, Chang Sukbok, Highly Stereoselective and Efficient Hydrosilylation of Terminal Alkynes Catalyzed by [RuCl2(p-cymene)]2, 10.1021/ol0059697
  59. Kawanami Yukio, Sonoda Yoshiya, Mori Takashi, Yamamoto Keiji, Ruthenium-Catalyzed Hydrosilylation of 1-Alkynes with Novel Regioselectivity, 10.1021/ol026089q
  60. Menozzi Candice, Dalko Peter I., Cossy Janine, Hydrosilylation of Terminal Alkynes with Alkylidene Ruthenium Complexes and Silanes, 10.1021/jo051637+
  61. Kim Hyunwoo, Ho Stephen, Leighton James L., A More Comprehensive and Highly Practical Solution to Enantioselective Aldehyde Crotylation, 10.1021/ja200712f
  62. Harrison Tyler J., Ho Stephen, Leighton James L., Toward More “Ideal” Polyketide Natural Product Synthesis: A Step-Economical Synthesis of Zincophorin Methyl Ester, 10.1021/ja201467z
  63. Harrison Tyler J., Rabbat Philippe M. A., Leighton James L., An “Aprotic” Tamao Oxidation/Syn-Selective Tautomerization Reaction for the Efficient Synthesis of the C(1)–C(9) Fragment of Fludelone, 10.1021/ol302221s
  64. Reznik Samuel K., Marcus Brian S., Leighton James L., Complex fragment coupling by crotylation: a powerful tool for polyketide natural product synthesis, 10.1039/c2sc21325g
  65. Reznik Samuel K., Leighton James L., Toward a more step-economical and scalable synthesis of spongistatin 1 to facilitate cancer drug development efforts, 10.1039/c3sc22186e
  66. Spletstoser Jared T., Zacuto Michael J., Leighton James L., Tandem Silylformylation−Crotylsilylation/Tamao Oxidation of Internal Alkynes: A Remarkable Example of Generating Complexity from Simplicity, 10.1021/ol802489w
  67. 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
  68. 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
  69. 4 a h
  70. Yamamoto Yoshihiko, Kirai Naohiro, Harada Yu, Cu-catalyzed stereoselective conjugate addition of arylboronic acids to alkynoates, 10.1039/b802231c
  71. Poli, Transition Metal Catalyzed Enantioselective Allylic Substitution in Organic Synthesis, 1 (2012)
  72. Trost Barry M., Weber Lothar, Strege Paul, Fullerton Terry J., Dietsche Thomas J., Allylic alkylation: nature of the nucleophile and application to prenylation, 10.1021/ja00479a026
  73. Nilsson Karolina, Andersson Thomas, Ullenius Christina, Gerold Andreas, Krause Norbert, NMR Spectroscopic Investigation of the Adducts Formed by Addition of Cuprates to Ynoates and Ynones: Alkenylcuprates or Allenolates?, 10.1002/(sici)1521-3765(19981002)4:10<2051::aid-chem2051>3.0.co;2-f
  74. Li Guigen, Wei Han-Xun, Whittlesey Bruce R., Batrice Nassim N., Novel Asymmetric C−C Bond Formation Process Promoted by Et2AlCl and Its Application to the Stereoselective Synthesis of Unusual β-Branched Baylis−Hillman Adducts, 10.1021/jo981976l
  75. Yeh Ming Chang P., Knochel Paul, The reactivity of the highly functionalized copper, zinc reagents RCu(CN)ZnI toward 1-haloalkynes and acetylenic esters, 10.1016/s0040-4039(01)80511-6
  76. Yamamoto Yoshinori, Yatagai Hidetaka, Maruyama Kazuhiro, Stereocontrolled cis addition of organocopper reagents RCu.cntdot.BR'3 to .alpha.,.beta.-acetylenic carbonyl compounds, 10.1021/jo01324a047
  77. Mueller Amanda J., Jennings Michael P., A Highly Stereoselective TMSOTf-Mediated Catalytic Carbocupration of Alkynoates, 10.1021/ol702546w
  78. Jennings Michael P., Sawant Kailas B., TMSCl-Mediated Catalytic Carbocupration of Alkynoates: An Unprecedented and Remarkable Effect of Catalyst Loading on Highly Selective Stereochemical Induction via a TMS-Allenoate Intermediate, 10.1002/ejoc.200400314
  79. Klein Joseph, Levene Raphael, Two different structures for copper and lithium derivatives of vinylic enolates. The effect of structure on the direction of electrophilic attack, 10.1039/p29730001971
  80. Marino Joseph P., Linderman Russell J., Chemistry of substituted (.alpha.-carbethoxyvinyl)cuprates. 2. Stereospecific olefin synthesis, 10.1021/jo00172a036
  81. Ahlquist Mårten, Nielsen Thomas E., Le Quement Sebastian, Tanner David, Norrby Per-Ola, An Experimental and Theoretical Study of the Mechanism of Stannylcupration of α,β-Acetylenic Ketones and Esters, 10.1002/chem.200501229
  82. Castaño Ana M., Ruano María, Echavarren Antonio M., Palladium-switchable bisnucleophiles, 10.1016/0040-4039(96)01407-4
  83. Castaño Ana M., Méndez María, Ruano María, Echavarren Antonio M., Reaction of Vinyl Epoxides with Palladium-Switchable Bisnucleophiles:  Synthesis of Carbocycles, 10.1021/jo0056850