Metal-free dihydroxylation of alkenes using cyclobutane malonoyl peroxide

Journal of Organic Chemistry

Volumn 77, Issue 2, 2012, Pages 921-928

  Jones, Kevin M ^a   Tomkinson, Nicholas C O ^b  

^a CARDIFF UNIVERSITY   (United Kingdom)

^b UNIVERSITY OF STRATHCLYDE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALINE HYDROLYSIS; ALLYLIC ALCOHOL; CHLOROFORM SOLUTIONS; CYCLOBUTANES; DIHYDROXYLATION; REACTION PATHWAYS; SINGLE-STEP;

BUTANE; DEUTERIUM; HYDROXYLATION; OXIDATION; SYNTHESIS (CHEMICAL);

OLEFINS;

5 (2 HYDROXYPHENYL) 3,3 SPIROCYCLOBUTYLBUTYROLACTONE; 5 (4 HYDROXYPHENYL) 3,3 SPIROCYCLOBUTYLBUTYROLACTONE; 5 (4 N BOC PHENYL) 3,3 SPIROCYCLOBUTYLBUTYROLACTONE; ALCOHOL; ALKENE; ALLYL COMPOUND; CYCLOBUTANE; DEUTERIUM; GAMMA LACTONE DERIVATIVE; MALONOYL PEROXIDE; OXYGEN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; DIHYDROXYLATION; HYDROLYSIS; STEREOCHEMISTRY;

EID: 84856116141     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo202084w     Document Type: Article

References (64)

1. Transition metals for Organic Synthesis, 2 nd ed.; Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, Germany, 2004.
2. Comprehensive Organic Synthesis: Selectivity, Strategy and Efficiency in Modern Organic Chemistry; Ley, S. V., Ed.; Pergamon: Oxford, U. K., 1992; Vol. 7, Oxidation.
3. Modern Heterogeneous Oxidation Catalysis; Mizuno, N., Ed.; Wiley-VCH: Weinheim, Germany, 2009.
4. Heterogeneous Hydrocarbon Oxidation; Warren, B. K., Oyama, S. T., Eds.; American Chemical Society: Washington, D. C., 1996; ACS Symposium series, Vol. 638.
5. Busch, D. H.; Alcock, N. W. Chem. Rev. 1994, 94, 585
6. Mennier, B. Chem. Rev. 1992, 92, 1411
7. The Activation of Dioxygen and Homogeneous Catalytic Oxidation; Barton, D. H. R.; Martell, A. E.; Sawyer, D. T., Eds.; Plenum Press: New York, 1993.
8. Simandi, L. Catalytic Activation of Dioxygen by Metal Complexes; Kluwer Academic Publisher: Dordrecht, The Netherlands, 1992.
9. Hill, C. L. Activation and Functionalization of Alkanes; Academic Press: New York, 1989.
10. Sheldon, R. A.; Kochi, J. K. Metal-Catalyzed Oxidations of Organic Compounds; Academic Press: New York, 1981.
11. Modern Oxidation Methods; Bäckvall, J.-E., Ed.; Wiley-VCH: Weinheim, Germany, 2004.
12. Muirhead-Hofmann, K. M.;; Reeve, T. B.;; Russell, A. G.;; Smith, M. H.;; Weston, M.;; White, M. J. SOS Reagents: Oxidation; Georg Thieme Verlag KG: Stuttgart, New York, 2010.
13. Criegee, R. Justus Liebigs Ann. Chem. 1936, 522, 75
14. Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483
15. Dobler, C.; Mehltretter, G. M.; Sundermeier, U.; Beller, M. J. Organomet. Chem. 2001, 621, 70
16. Christie, S. D. R.; Warrington, A. D. Synthesis 2008, 1325
17. Asghar, S. F.; Lewis, S. E. Annu. Rep. Prog. Chem., Sect. B: Org. Chem. 2011, 107, 34
18. Li, Y.; Song, D.; Dong, V. M. J. Am. Chem. Soc. 2008, 130, 2962
19. Wang, A.; Jiang, H.; Chen, H. J. Am. Chem. Soc. 2009, 131, 3846
20. Wang, W.; Wang, F.; Shi, M. Organometallics 2010, 29, 928
21. Chen, K.; Costas, M.; Kim, J.; Tipton, A. K.; Que, L., Jr. J. Am. Chem. Soc. 2002, 124, 3026
22. Oldenburg, P. D.; Que, L., Jr. Catal. Today 2006, 117, 15
23. Plietker, B.; Niggemann, A.; Pollrich, A. Org. Biomol. Chem. 2004, 2, 1116
24. Plietker, B.; Niggemann, A. J. Org. Chem. 2005, 70, 2402
25. Neisius, N. M.; Plietker, B. J. Org. Chem. 2008, 73, 3218
26. Boer, J. W.; Brinksma, J.; Browne, W. R.; Meetsma, A.; Alsters, P. L.; Hage, R.; Feringa, B. L. J. Am. Chem. Soc. 2005, 127, 7990
27. Boer, J. W.; Brinksma, J.; Browne, W. R.; Harutyunyan, S. R.; Bini, L.; Tiemersma-Weyman, T. D.; Alsters, P. L.; Hage, R.; Feringa, B. L. Chem. Commun. 2008, 3747
28. Seayad, J.; Seayad, A. M.; Chai, C. L. L. Org. Lett. 2010, 12, 1412
29. Bataille, C. J. R.; Donohoe, T. J. Chem. Soc. Rev. 2011, 40, 114
30. Schmidt, V. A.; Alexanian, E. J. Angew. Chem., Int. Ed. 2010, 49, 4491
31. Giglio, B. C.; Schmidt, V. A.; Alexanian, E. J. J. Am. Chem. Soc. 2011, 133, 13320
32. Fujita, M.; Wakita, M.; Sugimura, T. Chem. Commun. 2011, 47, 3983
33. Emmanuvel, L.; Shaikh, T. M. A.; Sudalai, A. Org. Lett. 2005, 7, 5071
34. Çelik, M.; Alp, C.; Coşkun, B.; Gültekin, M. S.; Balci, M. Tetrahedron Lett. 2006, 47, 3659
35. Santoro, S.; Santi, C.; Sabantini, M.; Testaferri, L.; Tieco, M. Adv. Synth. Catal. 2008, 350, 2881
36. Greene, F. D. J. Am. Chem. Soc. 1956, 78, 2246
37. Greene, F. D. J. Am. Chem. Soc. 1956, 78, 2250
38. Greene, F. D.; Rees, W. W. J. Am. Chem. Soc. 1958, 80, 3432
39. Greene, F. D. J. Am. Chem. Soc. 1959, 81, 1503
40. Greene, F. D.; Rees, W. W. J. Am. Chem. Soc. 1960, 82, 890
41. Greene, F. D.; Rees, W. W. J. Am. Chem. Soc. 1960, 82, 893
42. Tadokoro, A.; Takata, T.; Endo, T. Macromolecules 1993, 26, 2388
43. Yuan, C.; Axelrod, A.; Varela, M.; Danysh, L.; Siegel, D. Tetrahedron Lett. 2011, 52, 2540
44. Griffiths, J. C.; Jones, K. M.; Picon, S.; Rawling, M. J.; Kariuki, B. M.; Campbell, M.; Tomkinson, N. C. O. J. Am. Chem. Soc. 2010, 132, 14409
45. Greene, F. D.; Rees, W. W. J. Am. Chem. Soc. 1957, 80, 3432
46. Adam, W.; Rucktäschel, R. J. Am. Chem. Soc. 1971, 98, 557
47. Heaney, H Aldrichimica Acta 1993, 26, 35
48. Alberts, A. H.; Wynberg, H.; Strating, J. Synth. Commun. 1973, 3, 297
49. Darmon, M. J.; Schuster, G. B. J. Org. Chem. 1982, 47, 4658
50. Porter, J. E.; Schuster, G. B. J. Org. Chem. 1985, 50, 4068
51. Smith, M. B.; March, J. In March's Advanced Organic Chemistry, 5 th ed.; John Wiley & Sons: New York, 2001; pp 1541-1542.
52. Grennberg, H.; Bäckvall, J.-E. Allylic Oxidations: Palladium-Catalyzed Allylic Oxidation of Olefins; Wiley-VCH Verlag GmbH & Co: Weinheim, Germany, 2004; Vol. 2, p 243.
53. Moiseev, I. I.; Vargaftik, M. N. Coord. Chem. Rev. 2004, 248, 2381
54. Andrus, M. B.; Lashley, J. C. Tetrahedron 2002, 58, 845
55. Chapman, O. L.; Wojtkowski, P. W.; Adam, W.; Rucktäschel, R. R. J. Am. Chem. Soc. 1972, 94, 1365
56. Franzen, V.; Driesen, H. E. Chem. Ber. 1963, 96, 1881
57. Wang, Z. J. Org. Chem. 2008, 73, 2270
58. Mo, J.; Xu, L.; Ruan, J.; Liu, S.; Xiao, J. Chem. Commun. 2006, 34, 3591
59. Kadyrov, R. Angew. Chem., Int. Ed. 2009, 48, 7556
60. Nicolaou, K. C. Chem.-Eur. J. 2004, 10, 5581
61. Nicolaou, K. C.; Snyder, S. A.; Longbottom, D. A.; Nalbandian, A. Z.; Huang, X. Chem.-Eur. J. 2004, 10, 5581
62. Medlik-Balan, A. Tetrahedron 1980, 36, 299
63. Fuganti, C. Chem. Ind. (London, U. K.) 1977, 24, 983
64. Edin, M. Tetrahedron: Asymmetry 2006, 17, 708