Allylsilanes and vinylsilanes from silylcupration of carbon - Carbon multiple bonds: Scope and synthetic applications

Accounts of Chemical Research

Volumn 37, Issue 10, 2004, Pages 817-825

  Barbero, Asunción ^a,b,c   Pulido, Francisco J ^a,b,c,d  

^a UNIVERSITY OF VALLADOLID   (Spain)

^b University of Valladolid ^*  (Spain)

^c UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^d Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE DERIVATIVE; ALLENE DERIVATIVE; ALLYL COMPOUND; CARBON; HETEROCYCLIC COMPOUND; NATURAL PRODUCT; SEROTONIN ANTAGONIST; SILANE DERIVATIVE; STYRENE DERIVATIVE; VINYL DERIVATIVE;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CYCLIZATION; CYCLOADDITION; METHODOLOGY; STEREOCHEMISTRY; SYNTHESIS;

EID: 6944249016     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar0400490     Document Type: Article

References (76)

1. (a) Fleming, I. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds; Pergamon: Oxford, U.K., 1991; Vol. 2, pp 563-593.
2. (b) Davies, A. G. In Comprehensive Organometallic Chemistry II; Pergamon: New York, 1995; Vol. 2, p 217.
3. (a) Sharma, S.; Oehlschlager, A. C. Synthetic and Mechanistic Implications of Ligand Mixing in Higher-Order Mixed (Trialkylsilyl)cuprates and (Trialkylstannyl)cuprates. J. Org. Chem. 1991, 56, 770-776.
4. 2. Tetrahedron 1988, 44, 4277-4292.
5. (c) Arnold, J.; Engeler, M. P.; Elsner, F. H.; Heyn, R. H.; Tilley, T. D. Insertion of Ethylene into Zr-Si and Hf-Si Bonds. Organometallics 1989, 8, 2284-2286.
6. (d) Wu, M.-Y.; Yang, F.-Y.; Cheng, C.-H. Carbosilylation of Allenes Catalysed by Palladium Complexes: A New Efficient Route to Substituted Allylic Silanes. J. Org. Chem. 1999, 64, 2471-2474.
7. (e) Horn, K. A. Regiochemical and Stereochemical Aspects of the Palladium-Catalyzed Reactions of Silanes. Chem. Rev. 1995, 95, 1317-1350.
8. (f) Sharma, H. K.; Pannell, K. H. Activation of the Si-Si Bond by Transition-Metal Complexes. Chem. Rev. 1995, 95, 1351-1374.
9. (g) Suginome, M.; Matsuda, T.; Nakamura, H.; Ito, Y. Regio and Stereoselective Synthesis of (Z)-β-Silylalkenylboranes by Silaboration of Alkynes Catalyzed by Palladium and Platinum Complexes. Tetrahedron. 1999, 55, 8787-8800.
10. (h) Suginome, M.; Ito, Y. Regio and Stereoselective Synthesis of Boryl-Substituted Allylsilanes via Transition Metal-Catalysed Silaboration. J. Organomet. Chem. 2003, 43-50.
11. (i) Barbero, A.; Pulido, F. J. Silyl- and Stannylcupration of Activated Multiple Bonds: Scope and Synthetic Applications. In Recent Research Developments in Synthetic Organic Chemistry, Pandalai, S. G., Ed.; Transworld Research Network: Trivandrum, India, 1999; Vol 2, Chapter 1.
12. (j) Krause, N. Modern Organocopper Chemistry, Wiley-VCH: Dortmund, Germany, 2002; pp 93-102.
13. Fleming, I.; Landais, Y.; Raithby, P. R. The Stereochemistry of the Silyl-Cupration of Allenes. J. Chem. Soc., Perkin Trans 1 1991, 715-719.
14. Fleming, I.; Pulido, F. J. The Synthesis of Allylsilanes and Vinylsilanes by Silyl-Cupration of Allenes. J. Chem. Soc., Chem. Commun. 1986, 1010-1011.
15. Fleming, I.; Rowley, M.; Cuadrado, P.; González-Nogal, A. M.; Pulido, F. J. The Silyl-Cupration and Stannyl-Cupration of Allenes. Tetrahedron 1989, 45, 413-424.
16. Blanco, F. J.; Cuadrado, P.; González, A. M.; Pulido, F. J.; Fleming, I. New Findings on the Regiochemistry of the Silylcupration of Allene. Tetrahedron Lett. 1994, 35, 8881-8882.
17. Liepins, V.; Karlström, S. E.; Bäckvall, J. E. Silylcupration of Allenes and Subsequent Electrophilic Trapping by Allylic Phosphates. A Novel Approach to Silylated 1,4-Diene Systems. Org. Lett. 2000, 2, 1237-1239.
18. Barbero, A.; Cuadrado, P.; González, A. M.; Pulido, F. J.; Fleming, I. The Reaction of tert-Butyldiphenylsilylcuprates with Allenes. J. Chem. Soc., Perkin Trans 1 1991, 2811-2816.
19. (a) Fleming, I.; Newton, T. W.; Roessler, F. The Silylcupration of Acetylenes. A Synthesis of Vinylsilanes. J. Chem. Soc., Perkin Trans 1 1981, 2527-2532.
20. (b) Barbero, A.; Cuadrado, P.; Fleming, I.; González, A. M.; Pulido, F. J.; Sánchez, A. Synthesis of Vinylsilanes by Silyl-Cupration of Acetylenes Using tert-Butyldiphenylsilylcuprate Reagents. J. Chem. Soc., Perkin Trans 1 1995, 1525-1532.
21. (c) Liepins, V.; Karlström, A. S. E.; Bäckvall, J.-E. Allylic Phosphates and Allylic Phosphinates as Electrophiles in Efficient Silylcupration Reactions of Acetylenes. J. Org. Chem. 2002, 67, 2136-2143.
22. (d) Fleming, I.; Lawrence, N. J. Stereocontrol in Organic Synthesis Using Silicon-Containing Compounds. A Synthesis of a (±)-Carbacyclin Analogue with the Geometry of the Exocyclic Double Bond Controlled by the Protodesilylation of an Allylsilane. J. Chem. Soc., Perkin Trans 1 1998, 2679-2686.
23. Capella, L.; Capperucci, G.; Curotto, G.; Lazzari, D.; Dembech, P.; Reginato, G.; Ricci, A. Silylcupration of N-Phenyl-N-ethynyl-aniline: A Versatile Route to Functionalized N,N-Bis(phenyl)-enamines. Tetrahedron Lett. 1993, 34, 3311-3314.
24. Casarini, A.; Jousseaume, B.; Lazzari, D.; Porciatti, E.; Reginato, G.; Ricci, A.; Seconi, G. The Stannyl-Cupration and Silyl-Cupration of Propargylic Sulfides. Synlett 1992, 981-982.
25. (a) Taber, D. F.; Bhamidipati, R. S.; Yet, L. Phenyldimethylsilyl as an Alcohol Surrogate in Intramolecular Diels-Alder Cycloaddition: Synthesis of α-Dictyopterol. J. Org. Chem. 1995, 60, 5537-5539.
26. (b) Denmark, S. E.; Thorarensen, A. Tandem [4 + 2]/[3 + 2) Cycloadditions of Nitroalkenes. The Synthesis of (+)-Crotanecine. J. Am. Chem. Soc. 1997, 119, 125-137.
27. (a) Reginato, G.; Mordini, A.; Valacchi, M.; Grandini, E. Silylcupration of (R)-2,2-Dimethyl-3-(tert-butoxycarbonyl)-4-ethynyloxazolidine: A Stereoselective Approach to the Synthesis of γ-Silylated Saturated and Unsaturated α-Amino Acids. J. Org. Chem. 1999, 64, 9211-9216.
28. (b) Ricci, A.; Blart, E.; Comes-Francini, M.; Reginato, G.; Zani, P. Regio- and Stereoselective Metal-Mediated Synthesis of Polyfunctionalized Alkenes. Pure Appl. Chem. 1996, 68, 679-682.
29. Fleming, I.; Martínez de Marigorta, E. Silyl-Cupration of an Acetylene Followed by Ring-Formation. J. Chem. Soc., Perkin Trans 1 1999, 889-900.
30. (a) Liepins, V.; Bäckvall, J. E. Silylcupration of 1,3-Dienes Followed by an Electrophilic Trapping Reaction. Org. Lett. 2001, 3, 1861-1864.
31. (b) Liepins, V.; Bäckvall, J. E. Regioselective 1,4-Silylcupration of 1,3-Dienes - Characterization and Electrophilic Trapping of the Intermediate (σ-Allyl)copper Complex, Eur. J. Org. Chem. 2002, 21, 3527-3535.
32. (a) Liepins, V.; Bäckvall, J. E. Silylcupration of Styrenes Followed by Electrophilic Trapping Reaction. Chem. Commun. 2001, 265-266.
33. (b) Woodward, S. Decoding the Black Box Reactivity that is Organocuprate Conjugate Addition Chemistry. Chem. Soc. Rev. 2000, 29, 393-401.
34. Furstner, A.; Brehm, C.; Cancho-Grande, Y. Stereoselective Synthesis of Enamides by a Peterson Reaction Manifold. Org. Lett. 2001, 3, 3955-3957.
35. Barbero, A.; Blanco, Y.; García, C.; Pulido, F. J. The Peterson Olefination Using the tert-Butyldiphenylsilyl Group: Stereoselective Synthesis of Di- and Trisubstituted Alkenes. Synthesis 2000, 1223-1228.
36. (a) Tietze, L. F.; Neumann, T.; Kajino, M.; Pretor, M. Efficient Synthesis of Branched Propargyl- and Allylsilanes. Synthesis 1995, 1003-1006.
37. (b) Enders, D.; Bhushan, V.; Lohray, B. B. Efficient Enantioselective Synthesis of Allylsilanes by Wittig Olefination of α-Silylaldehydes. Tetrahedron Lett. 1993, 34, 5067-5070.
38. Enders, D. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: Orlando, FL 1984; Vol. 3, p 275.
39. Chaunet, D. C.; Chang, J. M. Reactions of α-Epoxysilanes with Organocopper Reagents. A Stereoselective Route to Alkenes. Tetrahedron Lett. 1993, 34, 3695-3698.
40. Hudrlik, P. F.; Kulkarni, A. K. α-Silylaldehydes: Preparation and Use as Stereoselective Vinyl Cation Equivalents. J. Am. Chem. Soc. 1981, 103, 6251-6253.
41. (a) Contrary to other reported, examples where the Stork-Colvin reaction occurs predominantly under these conditions are given in the following: Stork, G.; Colvin, E. New Synthesis of Aldehydes via Vinylsilanes. J. Am. Chem. Soc. 1971, 93, 2080-2081. (b) The acid-catalyzed rearrangement of 2-tert-butyldiphenyl-1,2-epoxy-hexane gives 1-tert-butyldiphenylsilylhexan-2- one, which can only be explained if cleavage of the C-O bond β to silicon takes place.
42. (a) Contrary to other reported, examples where the Stork-Colvin reaction occurs predominantly under these conditions are given in the following: Stork, G.; Colvin, E. New Synthesis of Aldehydes via Vinylsilanes. J. Am. Chem. Soc. 1971, 93, 2080-2081. (b) The acid-catalyzed rearrangement of 2-tert-butyldiphenyl-1,2-epoxy-hexane gives 1-tert-butyldiphenylsilylhexan-2- one, which can only be explained if cleavage of the C-O bond β to silicon takes place.
43. Fleming, I.; Lawrence, N. J. Stereocontrol in Organic Synthesis Using Silicon-Containing Compounds. A Synthesis of (-) Tetrahydrolipstatin Using the Alkylation of a β-Silyl Ester and the Hydroboration of an Allylsilane. J. Chem. Soc., Perkin Trans. 1 1998, 2679-2686.
44. Mandal, A. K. Stereocontrolled Total Synthesis of (-)-Ebelactone A. Org. Lett. 2002, 4, 2043-2045.
45. (a) Beller, M.; Bolm, C. Transition Metals for Organic Synthesis; Wiley-VCH: Weinheim, Germany, 1998.
46. (b) Diederich, F.; Stang, P. J. Metal-catalysed Cross-coupling Reactions; Wiley-VCH: Weinheim, Germany, 1998.
47. 7 (a) Jabri, N.; Alexakis, A.; Normant, J. P. Alkenyl-Copper Derivatives 19. Synthesis of Conjugated Dienes and Styrenes by Coupling of Alkenyl Cuprates with Alkenyl and Aryl Halides. Bull. Soc. Chim. Fr. 1983, 321-331.
48. (b) Gardette, M.; Jabri, N.; Alexakis, A.; Normant, J. F. General Methodology for the Synthesis of Conjugated Dienic Insect Sex-Pheromones. Tetrahedron 1984, 2741-2750.
49. Barbero, A.; García, C.; Pulido, F. J. Allylsilane-Vinylcopper Reagents: Palladium-Mediated Coupling with Alkenyl Halides. Synthesis and Photochemical [2 + 2] Cyclization of (±)-lpsdienol. Synlett 2001, 824-826.
50. Barbero, A.; García, C.; Pulido, F. J. Silylcupration of Allenes Followed by Reaction with Enones. A New Strategy for the Synthesis of Methylenecyclopentanols. Tetrahedron Lett. 1999, 40, 6649-6652.
51. Barbero, A.; García, C.; Pulido, F. J. Functionalised Allylsilanes from Silylcopper Reagents and Allene. A Useful Strategy for Cyclopentane Annulations. Tetrahedron 2000, 56, 2739-2751.
52. Suginome, M.; Iwanami, T.; Yamamoto, A.; Ito, Y. Asymmetric Synthesis of Cyclic Alkenes via Cyclization of Enantioenriched Allylsilanes. Synlett 2001, 1042-1045.
53. Barbero, A.; Blanco, Y.; Pulido, F. J. A Tandem Allylsilane-Vinylsilane Difunctionalization by Silylcupration of Allene Followed by Reaction with α,β-Unsaturated Nitriles. Chem. Commun. 2001, 1606-1607.
54. (a) Fleming, I.; Barbero, A.; Walter, D. Stereochemical Control in Organic Synthesis Using Silicon-Containing Compounds. Chem. Rev. 1997, 97, 2063-2192.
55. (b) Denmark, S. E.; Fu, J. Catalytic Enantioselective Addition of Allylic Organometallic Reagents to Aldehydes and Ketones. Chem. Rev. 2003, 103, 2763-2793.
56. (c) Veenstra, S. J.; Schmid, P. One-Pot Synthesis of Protected Homoallyl Amines. Tetrahedron Lett. 1997, 38, 997-1000.
57. (d) Yanagisawa, A.; Morodome, M.; Nakashima, H.; Yamamoto, H. Allylation of Aldehydes with Allyltin Compounds in Acidic Aqueous Media. A Catalytic Version. Synlett 1997, 1309-1311.
58. 3-Catalyzed Three-Component Reactions of Aldehydes, Amines and Allyltributylstannane in Micellar Systems. Facile Synthesis of Homoallylic Amines in Water. Chem. Commun. 1998, 19-20.
59. (b) Kobayashi, S.; Iwamoto, S.; Nagayama, S. Group 4 Metal Triflates as Efficient Catalysts for Allylations of Imines with Allyltributylstannane and Mannich-Type Reactions of Imines with Silyl Enol Ethers. Synlett 1997, 1099-1101.
60. (c) Hachiya, I.; Kobayashi, S. Aqueous Reactions with a Lewis Acid and an Organometallic Reagent. The Scandium Trifluoromethanesulfonate-Catalyzed Allylation Reaction of Carbonyl Compounds with Tetraallyltin. J. Org. Chem. 1993, 58, 6958-6960.
61. Yadav, J. S.; Chand, P. K.; Anjaneyulu, S. Iodine-Catalysed Allylation of Aldehydes with Allyltrimethylsilane. Tetrahedron Lett. 2002, 43, 3783-3784.
62. (a) Denmark, S. E.; Fu, J. P. Catalytic Enantioselective Allylation with Chiral Lewis Bases. Chem. Commun. 2003, 167-170.
63. (b) Denmark, S. E.; Fu, J. P. Catalytic, Enantioselective Addition of Substituted Allylic Trichlorosilanes Using a Rationally-Designed 2,2′-Bispyrrolidine-Based Bisphosphoramide. J. Am. Chem. Soc. 2001, 123, 9488-9489.
64. Denmark, S. E.; Fu, J. P. Asymmetric Construction of Quaternary Centers by Enantioselective Allylation: Application to the Synthesis of the Serotonin Antagonist LY426965. Org. Lett 2002, 4, 1951-1953.
65. Barbero, A.; Castreño, P.; García, C.; Pulido, F. J. Intramolecular Cyclization of tert-Butyldiphenylallylsilane Units and Carbonyl Groups: Allylsilane Terminated Cyclization Versus the Ene Reaction. J. Org. Chem. 2001, 66, 7723-7728.
66. Angle, S. R.; Belanguer, D. S.; El-Said, N. A. Stereoselective Synthesis of Tetrahydropyrans via Formal [4 + 2] Cycloaddition: A Comparison of Allylsilane and Crotylsilane. J. Org. Chem. 2002, 67, 7699-7705.
67. Angle, S. R.; El-Said, N. A. Stereoselective Synthesis of Tetrahydrofurans via Formal [3+2] Cycloaddition of Aldehydes and Allylsilanes. Formal Total Synthesis of the Muscarine Alkaloids (-)-Allomuscarine and (+)-Epimuscarine. J. Am. Chem. Soc. 2001, 124, 3608-3613.
68. (a) Wang, D.; Chan, T.-H. Synthesis of Karahanaenol from Geraniol via an Allylsilane. J. Chem. Soc., Chem. Commun. 1984, 1273-1275.
69. (b) Armstrong, R. J.; Weiler, L. Synthesis of (±)-Karahana Ether and a (±)-Labdadienoic Acid by the Electrophilic Cyclization of Epoxy Allylsilanes. Can. J. Chem. 1986, 64, 584-596.
70. (c) Langer, P.; Holtz, E. Olefin Cross-Metathesis of Alkenyl Epoxides with Allyl- and Vinyl-Trimethylsilane. Synlett 2002, 110-112.
71. (d) Overman, L. E.; Renhowe, P. A. Regioselective Opening of Terminal Epoxides with 2-(Trialkylsilyl)allyl Organometallic Reagents. J. Org. Chem. 1994, 59, 4138-4142.
72. (a) Proctor, G.; Russell, A. T.; Murphy, P. J.; Tan, T. S.; Mather, A. N. Epoxy-Silanes in Organic Synthesis. Tetrahedron 1988, 44, 3953-3973.
73. (b) Molander, G. A.; Andrews, S. W. Regiochemical Control in the Intramolecular Addition of Allylstannanes and Allylsilanes to 2,3-Epoxy Ethers: Preparation of Functionalized Oxepanes. J. Org. Chem. 1989, 54, 3114-3120.
74. Barbero, A.; Castreño, P.; Pulido, F. J. Acid-Catalyzed Cyclization of Epoxyallylsilanes. An Unusual Rearrangement Cyclization Process. Org. Lett. 2003, 5, 4045-4048.
75. Corey, E. J.; Staas, D. D. Demonstration of a Common Concerted Mechanistic Pathway for the Acid-Catalyzed Cyclization of 5,6-Unsaturated Oxiranes in Chemical and Enzymatic Systems. J. Am. Chem. Soc. 1998, 120, 3526-3527.
76. Schlosser, M.; Franzini, L.; Bauer, C.; Leroux, F. About the Stereoelectronics of the Intramolecular Addition of Allylsilanes to Aldehydes. Chem.-Eur. J. 2001, 7, 1909-1914.