Tandem oxidation processes using manganese dioxide: Discovery, applications, and current studies

Accounts of Chemical Research

Volumn 38, Issue 11, 2005, Pages 851-869

  Taylor, Richard J K ^a   Reid, Mark ^a   Foot, Jonathan ^a,b   Raw, Steven A ^a,c  

^a UNIVERSITY OF YORK   (United Kingdom)

^b AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

^c ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 28844466070     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar050113t     Document Type: Article

References (77)

1. Taylor, R. J. K; Alcaraz, L.; Kapfer-Eyer, I.; Macdonald, G.; Wei, X.; Lewis, N. J. The Synthesis of Alisamycin, Nisamycin, LL-C10037α, and Novel Epoxyquinol and Epoxyquinone Analogues of Manumycin A. Synthesis 1998, 775-790.
2. Macdonald, G.; Alcaraz, L.; Wei, X.; Lewis, N. J.; Taylor, R. J. K. Unsaturated Amides Derived from 2-Amino-3-hydroxycyclopentenone: A Stille Approach to Asuka mABA, 2880-II, and Limocrocin. Tetrahedron 1998, 54, 9823-9836.
3. Alcaraz, L.; Macdonald, G.; Ragot, J.; Lewis, N. J.; Taylor, R. J. K. Manumycin A: Revision of Structure and Synthesis of the (+)-Enantiomer. J. Org. Chem. 1998, 63, 3526-3B27.
4. Alcaraz, L.; Macdonald, G.; Ragot, J.; Lewis, N. J.; Taylor, R. J. K. Synthetic Approaches to the Manumycin A, B, and C Antibiotics: The First Total Synthesis of (+)-Manumycin A. Tetrahedron 1999, 55, 3707-3716.
5. Meyers, A. I.; Babiak, K. A.; Campbell, A. L.; Comins, D. L.; Fleming, M. P.; Henning, R.; Heuschmann, M.; Hudspeth, J. P.; Kane, J. M.; Reider, P. J.; Roland, D. M.; Shimizu, K.; Tomioka, K.; Walkup, R. D. Total synthesis of (-)-Maysine. J. Am. Chem. Soc. 1983, 105, 5015-5024.
6. Ireland, R. E.; Norbeck, D. W. Application of the Swern Oxidation to the Manipulation of Highly Reactive Carbonyl Compounds. J. Org. Chem. 1985, 50, 2198-2200.
7. n Type via Iterative Hydrozirconation-Palladium-Catalyzed Cross-Coupling. Org. Lett. 2002, 4, 703-706.
8. Wei, X.; Taylor, R. J. K. In Situ Manganese Dioxide Alcohol Oxidation-Wittig Reactions: Preparation of Bifunctional Dienyl Building Blocks. J. Org. Chem. 2000, 65, 616-620.
9. MacCoss, R. N.; Balskus, E. P.; Ley, S. V. A Sequential Tetra-N-propylammonium Perruthenate (TPAP)-Wittig Oxidation-Olefination Protocol. Tetrahedron Lett. 2003, 44, 7779-7781.
10. Bressette, A. R.; Glover, L. C., III A Convenient One-Pot PCC Oxidation-Wittig Reaction of Alcohols. Synlett 2004, 738-740.
11. Tietze, L. F. Domino Reactions in Organic Synthesis. Chem. Rev. 1996, 96, 115-136.
12. Huang, C. C. Synthesis of C-14 Labelled 1-(4-Methoxybenzoyl)-5-oxo-2- pyrrolidinepropanoic Acid (CI-933). J. Labelled Compd. Radiopharm. 1987, 24, 676-681.
13. (a) Barrett, A. G. M.; Hamprecht, D.; Ohkubo, M. Dess-Martin Periodinane Oxidation of Alcohols in the Presence of Stabilized Phosphorus Ylides. J. Org. Chem. 1997, 62, 9376-9378.
14. (b) For the extension of this method to the direct olefination of silyl ethers, see Deng, G.; Xu, B.; Liu, C. DMP-Mediated One-Pot Oxidative Olefination of Silyl Ethers. Tetrahedron 2005, 61, 5818-5821.
15. 4 System. J. Org. Chem. 1998, 63, 4489-4493.
16. Crich, D.; Mo, X.-S. One-Pot Selective 5′-Oxidation/Olefination of 2′-Deoxynucleosides. Synlett 1999, 67-68.
17. Maiti, A.; Yadav, J. S. One-Pot Oxidation and Wittig Olefination of Alcohols using O-lodoxybenzoic Acid and Stable Wittig Ylides. Synth. Commun. 2001, 31, 1499-1506.
18. Kim, G.; Lee, D. G.; Chang, S. In Situ Aerobic Alcohol Oxidation-Wittig Reactions. Bull. Korean Chem. Soc. 2001, 22, 943-944.
19. Shet, J.; Desai, V.; Tilve, S. Domino Primary Alcohol Oxidation-Wittig Reaction. Synthesis 2004, 1859-1863.
20. Ball, S.; Goodwin, T. W.; Morton, R. A. Studies on Vitamin A. Biochem. J. 1948, 42, 516-523.
21. Fatiadi, A. J. Active Manganese Dioxide Oxidation in Organic Chemistry. Synthesis 1976, 65-104 and 133-167.
22. (a) Paquette, L. A. Manganese Dioxide; Encyclopedia of Reagents for Organic Synthesis; John Wiley and Sons: New York; Vol. 5, pp 3229-3235.
23. (b) Cahiez, G.; Alami, M. Manganese Dioxide (article RM021); Encyclopedia of Reagents for Organic Synthesis [Online]; John Wiley and Sons: New York, 2001.
24. (c) Taylor, R. J. K.; Foot, J. S.; Reid, M. Manganese Dioxide (article RM021); Encyclopedia of Reagents for Organic Synthesis [Online]; John Wiley and Sons: New York, 2004.
25. 2 recycling.
26. Kim, S. Y.; Park, K. H.; Chung, Y. K. Manganese(IV) Dioxide-Catalyzed Synthesis of Quinoxalines under Microwave Irradiation. Chem. Commun. 2005, 1321-1323.
27. Graham, S. H.; Jonas, D. A. Studies on Bicyclononanes. J. Chem. Soc. 1969, 188-194.
28. Wei, X.; Taylor, R. J. K. In Situ Alcohol Oxidation-Wittig Reactions. Tetrahedron Lett. 1998, 39, 3815-3818.
29. Petroski, R. J. Straightforward Preparation of (2E,4Z)-2,4-Heptadien-1-ol and (2E,4Z)-2,4-Heptadienal. Synth. Commun. 2003, 33, 3233-3241.
30. Khrimian, A. The Geometric Isomers of Methyl 2,4,6-Decatrienoate, Including the Pheromones of at Least Two Species of Stink Bugs. Tetrahedron 2005, 61, 3651-3657.
31. Nicolaou, K. C.; Li, Y.; Fylaktakidou, K. C.; Monenschein, H.; Li, Y.; Weyershausen, B.; Mitchell, H. J.; Wei, H.-X.; Guntupalli. P.; Hepworth, D.; Sugita, K. Total synthesis of Apoptolidin. J. Am. Chem. Soc. 2003, 125, 15433-15442.
32. Mladenova, M.; Tavlinova, M.; Momchev, M.; Alami, M.; Ourévitch, M.; Brion, J. D. An Iterative Procedure for the Synthesis of Conjugated Omega-Chlorotrienoic and -Tetraenoic Esters and Related Derivatives. Eur. J. Org. Chem. 2003, 2713-2718.
33. Aitken, D. J.; Faure, S.; Roche, S. Synthetic Approaches to the Southern Part of Cyclotheonamide C. Tetrahedron Lett. 2003, 44, 8827-8830.
34. (a) Blackburn, L.; Taylor, R. J. K. Unpublished results,
35. (b) Blackburn, L. Ph.D. Thesis, University of York, York, U.K., 2001.
36. Frederico, D.; Donate, P. M.; Constantino, M. G.; Bronze, E. S.; Sairre, M. I. A Short and Efficient Synthesis of Crocetin-Dimethyl Ester and Crocetindial. J. Org. Chem. 2003, 68, 9126-9128.
37. McDermott, P. J.; Stockman, R. A. Combining Two-Directional Synthesis and Tandem Reactions: Synthesis of Trioxadispiroketals. Org. Lett. 2005, 7, 27-29.
38. Blackburn, L.; Kanno, H.; Taylor, R. J. K. In Situ Alcohol Oxidation-Wittig Reactions using N-Methoxy-N-methyl-2- triphenylphosphoranylidine)acetamide. Tetrahedron Lett. 2003, 44, 115-118.
39. Huang, Z.-Z.; Sun, R.-J. Novel Stereoselective Synthesis of (E)-α,β-Unsaturated Nitriles and Ketones by the Tandem Reaction of Deprotonation-Oxidation-Wittig Reaction from Phosphonium Salts. J. Chem. Res., Synop. 2003, 40-41.
40. Blackburn, L.; Wei, X.; Taylor, R. J. K. Manganese Dioxide can Oxidise Unactivated Alcohols Under in Situ Oxidation-Wittig Conditions. Chem. Commun. 1999, 1337-1338.
41. Davies, S. B.; McKervey, M. A. Convenient in Situ Synthesis of Nonracemic N-Protected β-Amino Aldehydes from β-Amino Acids. Tetrahedron Lett. 1999, 40, 1229-1232.
42. Wilfred, C. D.; Taylor, R. J. K. Tandem Oxidation Sequence to Prepare Ethyl (E)-4,5-Dioxohexadecenoate: A Formal Synthesis of Podoscyphic Acid. Synthetic Commun. 2005, in press.
43. Harrison, I. T. Oxidation of Saturated Alcohols by Manganese Dioxide. Proc. Chem. Soc. 1964, 110.
44. (a) Crawforth, C. M.; Blackburn, L.; Taylor, R. J. K. Unpublished results.
45. (b) Blackburn, L., Ph.D. Thesis, University of York, York, U.K., 2001.
46. Runcie, K. A.; Taylor, R. J. K. The in Situ Oxidation-Wittig Reaction of α-Hydroxyketones. Chem. Commun. 2002, 974-975.
47. Volonterio, A.; Ramirez de Arellano, C.; Zanda, M. Synthesis of 1,3,5-Trisubstituted Hydantoins. J. Org. Chem. 2005, 70, 2161-2170.
48. Outram, H. S.; Raw, S. A.; Taylor, R. J. K. In Situ Oxidative Diol Cleavage-Wittig Processes. Tetrahedron Lett. 2002, 43, 6185-6187.
49. Dunlap, N. K.; Mergo, W.; Jones, J. M.; Carrick, J. M. A General Procedure for a One-Pot Oxidative Cleavage/Wittig Reaction of Glycols. Tetrahedron Lett. 2002, 43, 3923-3925.
50. Blackburn, L.; Pei, C.; Taylor, R. J. K. In Situ Alcohol Oxidation-Wittig Reactions using Non-stabilised Phosphoranes. Synlett 2002, 215-218.
51. Ando, K. Preparations of Z-α,β-Unsaturated Amides by Using Horner-Wadsworth-Emmons Reagents. Synlett 2001, 1272-1274.
52. Ranatunge, R. R.; Augustyniak, M.; et al. Synthesis and Selective Cyclooxygenase-2 Inhibitory Activity of a Series of Novel, Nitric Oxide Donor-Containing Pyrazoles. J. Med. Chem. 2004, 47, 2180-2193.
53. Reid, M.; Rowe, D.; Taylor R. J. K. Two Carbon Homologated α,β-Unsaturated Aldehydes from Alcohols Using the in Situ Oxidation-Wittig Reaction. Chem. Commun. 2003, 2284-2285.
54. Raw, S. A.; Reid, M.; Roman, E.; Taylor, R. J. K. A Tandem Oxidation Procedure for the Conversion of Alcohols into 1,1-Dibromoalkenes. Synlett 2004, 819-822.
55. (a) Müller, S.; Liepold, B.; Roth, G. J.; Bestmann, H. J. An Improved One-Pot Procedure for the Synthesis of Alkynes from Aldehydes. Synlett 1996, 521-522.
56. (b) Ohira, S. Methanolysis of Dimethyl (1-Diazo-2-Poxpropylphosphonate). Synth. Commun. 1989, 19, 561-564.
57. Quesada, E.; Taylor, R. J. K. One-Pot Conversion of Activated Alcohols into Terminal Alkynes. Tetrahedron Lett. 2005, 46, 6473-6476.
58. Oswald, M. F.; Raw, S. A.; Taylor, R. J. K. Tandem Oxidation Processes for the Preparation of Functionalised Cyclopropanes. Org. Lett. 2004, 6, 3997-4000.
59. Murphy, W. S.; Wattanasin, S. Total Synthesis of (±)- Picropodophyllone. J. Chem. Soc., Perkin Trans. 1 1982, 271-275.
60. Oswald, M. F.; Raw, S. A.; Taylor, R. J. K. Tandem Oxidation Processes: A Combined Phosphorus- and Sulfur-Ylide Approach to Polysubstituted Cyclopropanes. Chem. Commun. 2005, 2253-2255.
61. Blackburn, L.; Taylor, R. J. K. In Situ Oxidation-Imine Formation-Reduction Routes from Alcohols to Amines. Org. Lett. 2001, 3, 1637-1639.
62. Kanno, H.; Taylor, R. J. K. Tandem Oxidation Processes: The Direct Conversion of Activated Alcohols into Oximes. Synlett 2002, 1287-1290.
63. Medvedeva, A. S.; Mareev, A. V.; Borisova, A. I.; Afonin, A. V. Solvent-free MW-Assisted Direct Conversion of 3-Tri-organosilyl-(germyl)-prop-2- yn-1-ols to Ynimines. Arkivoc 2003, 13, 157-165.
64. Kanno, H.; Taylor, R. J. K. A One-Pot Oxidation-Imine Formation-Reduction Route from Alcohols to Amines using Manganese Dioxide-Sodium Borohydride. Tetrahedron Lett. 2002, 43, 7337-7340.
65. (a) Raw, S. A.; Wilfred, C. D.; Taylor R. J. K. Preparation of Quinoxalines, Dihydropyrazines, Pyrazines, and Piperazines using Tandem Oxidation Processes. Chem. Commun. 2003, 2286-2287.
66. (b) Raw, S. A.; Wilfred, C. D.; Taylor R. J. K. Tandem Oxidation Processes for the Preparation of Nitrogen-Containing Heteroaromatic and Heterocyclic Compounds. Org. Biomol. Chem. 2004, 2, 788-796.
67. Mueller, J. A.; Goller, C. P.; Sigman, M. S. Elucidating the Significance of β-Hydride Elimination and the Dynamic Role of Acid/Base Chemistry in a Palladium-Catalyzed Aerobic Oxidation of Alcohols. J. Am. Chem. Soc. 2004, 126, 9724-9734 and references therein.
68. Robinson, R. S.; Taylor, R. J. K. Quinoxaline Synthesis from α-Hydroxy Ketones via a Tandem Oxidation Process using Catalysed Aerobic Oxidation. Synlett 2005, 1003-1005.
69. Bagley, M. C.; Hughes, D. D.; Sabo, H. M.; Taylor, P. H.; Xiong, X. One-Pot Synthesis of Pyridines or Pyrimidines by Tandem Oxidation- Heteroannulation of Propargylic Alcohols. Synlett 2003, 1443-1446.
70. Raw, S. A.; Taylor R. J. K. Highly Substituted Pyridines via Tethered Enamine-Imine Methodology. Chem. Commun. 2004, 508-509.
71. Wilfred, C. D.; Taylor, R. J. K. Preparation of 2-Substituted Benzimidazoles and Related Heterocycles Directly from Alcohols Using TOP Methodology. Synlett 2004, 1628-1630.
72. McAllister, G. D.; Wilfred, C. D.; Taylor, R. J. K. Tandem Oxidation Processes: The Direct Conversion of Activated Alcohols into Nitriles. Synlett 2002, 1291-1292.
73. Lai, G.; Bhamare, N. K.; Anderson, W. K. A One-Pot Method for the Efficient Preparation of Aromatic Nitriles from Aldehydes using Ammonia, Magnesium Sulfate, and Manganese Dioxide. Synlett 2001, 230-231.
74. Corey, E. J.; Gilman, N. W.; Ganem, B. E. New Methods for the Oxidation of Aldehydes to Carboxylic Acids and Esters. J. Am. Chem. Soc. 1968, 90, 5616-5617.
75. (b) Gilman, N. W. The preparation of carboxylic amides from aldehydes by oxidation. J. Chem. Soc., Chem. Commun. 1971, 733-734.
76. (a) Foot, J. S.; Kanno, H.; Giblin, G. M. P.; Taylor, R. J. K. Tandem Oxidation Processes: The Direct Conversion of Activated Alcohols into Esters and Amides. Synlett 2002, 1293-1295.
77. (b) Foot, J. S.; Kanno, H.; Giblin, G. M. P.; Taylor, R. J. K. Esters and Amides from Activated Alcohols Using Manganese(IV) Dioxide. Synthesis 2003, 1055-1064.