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Copper-catalyzed addition of nucleophilic silicon to aldehydes

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Cirriez, Virginie [UCL] Rasson, Corentin [UCL] Hermant, Thomas [UCL] Petrignet , J. [UCL] Díaz Álvarez , J. [UCL] Robeyns, Koen [UCL] Riant, Olivier [UCL]

How to train your silane: A new family of chiral copper(I) complexes that bear a bifluoride counteranion were prepared and used in the first example of the enantioselective transfer of a silyl group to an aldehyde. This procedure provides fast access to non-racemic α-hydroxysilanes in high enantioselectivities. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Document type Article de périodique (Journal article) – Article de recherche
Access type Accès restreint
Publication date 2013
Language Anglais
Journal information "Angewandte Chemie (International Edition)" - Vol. 52, no. 6, p. 1785-1788 (2013)
Peer reviewed yes
Publisher Wiley - V C H Verlag GmbH & Co. KGaA ((Germany) Weinheim)
issn 1433-7851
e-issn 1521-3773
Publication status Publié
Affiliation UCL - SST/IMCN/MOST - Molecules, Solids and Reactivity
Keywords Aldehydes ; Nucleophilic additions ; Silyl group ; Addition reactions ; Aldehydes ; Catalysis ; Copper ; Enantioselectivity ; Organic compounds ; Silicon ; Copper compounds ; Asymmetric catalysis ; Copper ; Nucleophilic addition ; Silicon ; Asymmetric catalysis ; Copper complexes ; Enantioselective ; High enantioselectivity
Links
  1. Chem. Rev. 2013
  2. Hartmann, Chim. Oggi, 29, 34 (2011)
  3. 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
  4. Vyas Devendra J., Oestreich Martin, Copper-Catalyzed SiB Bond Activation in Branched-Selective Allylic Substitution of Linear Allylic Chlorides, 10.1002/anie.201004658
  5. Vyas Devendra J., Oestreich Martin, Kupferkatalysierte Si-B-Bindungsaktivierung in der verzweigtselektiven allylischen Substitution linearer Allylchloride, 10.1002/ange.201004658
  6. 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
  7. 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
  8. 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
  9. Ohmura Toshimichi, Suginome Michinori, Silylboranes as New Tools in Organic Synthesis, 10.1246/bcsj.82.29
  10. Vyas Devendra J., Fröhlich Roland, Oestreich Martin, Activation of the Si−B Linkage: Copper-Catalyzed Addition of Nucleophilic Silicon to Imines, 10.1021/ol200509c
  11. Cirillo Pier F., Panek James S., RECENT PROGRESS IN THE CHEMISTRY OF ACYLSILANES. A REVIEW, 10.1080/00304949209356728
  12. Fleming Ian, Barbero Asuncion, Walter David, Stereochemical Control in Organic Synthesis Using Silicon-Containing Compounds, 10.1021/cr941074u
  13. Buynak John D., Strickland J. Byron, Lamb Grady W., Khasnis Dipti, Modi Seema, Williams Delena, Zhang Hongming, Thermal rearrangements of .alpha.-(acyloxy)silanes: formation of chiral precursors and migratory preference of silicon-based groups, 10.1021/jo00025a024
  14. Linderman Russell J., Ghannam Ameen, Badejo Ibraheem, Aryl-substituted cyclic homoaldol products derived from (.alpha.-alkoxybenzyl)trimethylsilanes, 10.1021/jo00017a041
  15. Huckins John R., Rychnovsky Scott D., Synthesis of Optically Pure Arylsilylcarbinols and Their Use as Chiral Auxiliaries in Oxacarbenium Ion Reactions, 10.1021/jo035260o
  16. Ireland Robert E., Varney Michael D., A chiral primary alcohol equivalent: silyl-assisted asymmetric induction in the ester enolate Claisen rearrangement, 10.1021/ja00324a043
  17. Avery Mitchell A., Jennings-White Clive, Chong Wesley K. M., Synthesis of a C,D-ring fragment of artemisinin, 10.1021/jo00269a008
  18. Panek James S., Sparks Michelle A., Allylic transpositions of homochiral C-1-acyloxy E-crotyl silanes: stereospecific synthesis of E-vinylsilanes, 10.1021/jo00308a011
  19. Cirillo Pier F., Panek James S., Studies Directed toward the Synthesis of (+)-Sesbanimide A: Construction of the AB-Ring System (A Formal Total Synthesis), 10.1021/jo00090a025
  20. Sakaguchi Kazuhiko, Mano Hiroyuki, Ohfune Yasufumi, Syntheses of optically active 2-substituted cyclopropanecar☐ylic acids from chiral α-hydroxysilane derivatives, 10.1016/s0040-4039(98)00759-x
  21. Kamimura Akio, Kaneko Yukio, Ohta Ayaki, Matsuura Kenji, Fujimoto Yasuo, Kakehi Akikazu, Kanemasa Shuji, Enantioselective preparation of 3,4,5-trisubstituted 4,5-dihydroisoxazoles and their stereoselective elaboration of 5-side chain, 10.1016/s0040-4020(02)01255-3
  22. Jacobi Peter A., Tassa Carlos, Enantioselective Syntheses of Ring-C Precursors of Vitamin B12. Substrate Control. A Novel Si-Assisted Elimination of Vinyl Bromides, 10.1021/ol036061u
  23. Sakaguchi Kazuhiko, Higashino Masato, Ohfune Yasufumi, Acid-catalyzed rearrangement of α-hydroxytrialkylsilanes, 10.1016/s0040-4020(03)00952-9
  24. Izzo Irene, Avallone Elvira, Corte Luca Della, Maulucci Nakia, De Riccardis Francesco, Asymmetric synthesis of N,O-diprotected (2S,3S)-N-methyl-δ-hydroxyisoleucine, noncoded amino acid of halipeptin A, 10.1016/j.tetasy.2004.02.008
  25. Perrone Sylvie, Knochel Paul, Highly Diastereoselective Preparation of (E)-Alkenylsilanes Bearing an α-Chiral Center, 10.1021/ol063097o
  26. Guintchin Boris K., Bienz Stefan, Enantioselective Synthesis of Di-, Tri-, and Tetrasubstituted Allenylsilanes, 10.1021/om049505e
  27. Buynak John D., Strickland J. Byron, Hurd Trace, Phan Andrew, The conversion of acyl silanes into chiral secondary alcohols, 10.1039/c39890000089
  28. Soderquist John A, Anderson Charles L, Miranda Edgar I, Rivera Isaac, Kabalka George W, Essentially homochiral 1-silyl alcohols from the reduction of aliphatic acylsilanes with chlorodiisopinocampheylborane, 10.1016/s0040-4039(00)97704-9
  29. Takeda Kei, Ohnishi Yuji, Koizumi Toru, Enantioselective Reduction of α,β-Unsaturated Acylsilanes by Chiral Lithium Amides, 10.1021/ol990574c
  30. Arai Noriyoshi, Suzuki Ken, Sugizaki Satoshi, Sorimachi Hiroko, Ohkuma Takeshi, Asymmetric Hydrogenation of Aromatic, Aliphatic, and α,β-Unsaturated Acyl Silanes Catalyzed by Tol-binap/Pica Ruthenium(II) Complexes: Practical Synthesis of Optically Active α-Hydroxysilanes, 10.1002/anie.200704696
  31. Arai Noriyoshi, Suzuki Ken, Sugizaki Satoshi, Sorimachi Hiroko, Ohkuma Takeshi, Asymmetric Hydrogenation of Aromatic, Aliphatic, and α,β-Unsaturated Acyl Silanes Catalyzed by Tol-binap/Pica Ruthenium(II) Complexes: Practical Synthesis of Optically Active α-Hydroxysilanes, 10.1002/ange.200704696
  32. Matsuo Jun-ichi, Hattori Yu, Ishibashi Hiroyuki, Brønsted Acid Catalyzed Asymmetric Reduction of Ketones and Acyl Silanes Using Chiralanti-Pentane-2,4-diol, 10.1021/ol1006532
  33. Tacke Reinhold, Hengelsberg Heidi, Zilch Harald, Stumpf Burghard, Enantioselective microbial reduction of 1,1-dimethyl-1-sila-cyclohexan-2-one with growing cells of the yeast Kloeckera corticis (ATCC 20109), 10.1016/0022-328x(89)85160-5
  34. An Ilhwan, Onyeozili Edith N., Maleczka Robert E., Enzymatic kinetic resolution of α-hydroxysilanes, 10.1016/j.tetasy.2010.02.030
  35. Panella Lavinia, Feringa Ben L., de Vries Johannes G., Minnaard Adriaan J., Enantioselective Rh-Catalyzed Hydrogenation of Enol Acetates and Enol Carbamates with Monodentate Phosphoramidites, 10.1021/ol051559c
  36. Bain Sukhamaya., Ijadi-Maghsoodi Sina., Barton Thomas J., Kinetics and mechanisms of .alpha.- and .beta.-eliminations of alkoxysilanes from saturated and unsaturated carbon frameworks, 10.1021/ja00216a039
  37. Page Philip C. Bulman, Klair Sukhbinder S., Rosenthal Stephen, Synthesis and chemistry of acyl silanes, 10.1039/cs9901900147
  38. SYNTHESIS OF ACYLSILANES FROM MORPHOLINE AMIDES. SYNTHESIS OF 1-(DIMETHYL(PHENYL)SILYL)PROPAN-1-ONE, 10.15227/orgsyn.084.0022
  39. 2009 Org. Synth. Coll. Vol. 11
  40. Hiyama Tamejiro, Obayashi Michio, Mori Ichiro, Nozaki Hitosi, Generation of metal-free silyl anions from disilanes and fluoride catalyst. Synthetic reactions with aldehydes and 1,3-dienes, 10.1021/jo00154a043
  41. O’Brien Jeannette M., Hoveyda Amir H., Metal-Free Catalytic C–Si Bond Formation in an Aqueous Medium. Enantioselective NHC-Catalyzed Silyl Conjugate Additions to Cyclic and Acyclic α,β-Unsaturated Carbonyls, 10.1021/ja203031a
  42. Barrett Anthony G. M., Hill Jason M., Wallace Eli M., Flygare John A., Recent Studies on the Peterson Olefination Reaction, 10.1055/s-1991-20867
  43. Barrett Anthony G.M., Hill Jason M., The synthesis of α-stannyl-silanes and their use in the formation of alkenes, 10.1016/s0040-4039(00)92687-x
  44. Berry Malcolm B., Griffiths Russell J., Sanganee Mahesh J., Steel Patrick G., Whelligan Daniel K., Silenes as novel synthetic reagents: identification of a practical method for silene generation and trapping, 10.1039/b404166f
  45. Chang Che-Chien, Kuo Yu-Hsien, Tsai Yeun-Min, The synthesis of carbohydrate-derived acylsilanes and their intramolecular free radical cyclizations with the formation of polyoxygenated cyclopentanes, 10.1016/j.tetlet.2009.04.032
  46. Rösch Lutz, Altnau Gerald, Otto Wolfgang Helmut, Facile Nucleophilic Silylation Reactions at Carbonyl Functionalities Using Trimethylsilylaluminum Compounds, 10.1002/anie.198105811
  47. Rösch Lutz, Altnau Gerald, Otto Wolfgang Helmut, Einfache nucleophile Silylierungsreaktionen an Carbonylfunktionen mit Trimethylsilylaluminium-Verbindungen, 10.1002/ange.19810930632
  48. Arnold John, Tilley T. Don, Insertion of organic carbonyls into the tantalum-silicon bond of (.eta.5-C5Me5)Cl3TaSiMe3. Preparation and characterization of the .alpha.-silylalkoxides (.eta.5-C5Me5)Cl3TaOCRR'SiMe3, 10.1021/ja00245a022
  49. Kleeberg Christian, Feldmann Evgenia, Hartmann Eduard, Vyas Devendra J., Oestreich Martin, Copper-Catalyzed 1,2-Addition of Nucleophilic Silicon to Aldehydes: Mechanistic Insight and Catalytic Systems, 10.1002/chem.201102367
  50. Suginome Michinori, Matsuda Takanori, Ito Yoshihiko, Convenient Preparation of Silylboranes, 10.1021/om000254t
  51. Gulliver D.J., Levason W., Webster M., Coordination stabilised copper(I) flouride. Crystal and molecular structure of fluorotris(triphenylphosphine)copper(I)·ethanol (1/2), Cu(PPh3)3, P·2EtOH, 10.1016/s0020-1693(00)88590-4
  52. Hibbert Frank, Emsley John, Hydrogen Bonding and Chemical Reactivity, Advances in Physical Organic Chemistry (1990) ISBN:9780120335268 p.255-379, 10.1016/s0065-3160(08)60047-7
  53. Vergote Thomas, Nahra Fady, Welle Alexandre, Luhmer Michel, Wouters Johan, Mager Nathalie, Riant Olivier, Leyssens Tom, Unprecedented Copper(I) Bifluoride Complexes: Synthesis, Characterization and Reactivity, 10.1002/chem.201102655
  54. Tsuboi Sadao, Ishii Naomi, Sakai Takashi, Tari Isao, Utaka Masanori, Oxidation of Alcohols with Electrolytic Manganese Dioxide. Its Application for the Synthesis of Insect Pheromones, 10.1246/bcsj.63.1888
  55. Bobbitt James M., Oxoammonium Salts. 6.14-Acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium Perchlorate:  A Stable and Convenient Reagent for the Oxidation of Alcohols. Silica Gel Catalysis, 10.1021/jo981322c
Bibliographic reference Cirriez, Virginie ; Rasson, Corentin ; Hermant, Thomas ; Petrignet , J. ; Díaz Álvarez , J. ; et. al. Copper-catalyzed addition of nucleophilic silicon to aldehydes. In: Angewandte Chemie (International Edition), Vol. 52, no. 6, p. 1785-1788 (2013)
Permanent URL http://hdl.handle.net/2078.1/126143