Osmium-mediated oxidative cyclizations: A study into the range of initiators that facilitate cyclization

Chemistry - An Asian Journal

Volumn 4, Issue 8, 2009, Pages 1237-1247

  Donohoe, Timothy J ^a   Wheelhouse, Katherine M P ^a   Lindsay Scott, Peter J ^a   Churchill, Gwydion H ^a   Connolly, Matthew J ^a   Butterworth, Sam ^a   Glossop, Paul A ^b  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

Author keywords

Catalysis; Heterocycles; Osmium; Pyrrolidines; Tetrahydro furans

Indexed keywords

CATALYST LOADINGS; CYCLIZATIONS; ENANTIOPURE; ENANTIOPURE PRODUCTS; FIVE-MEMBERED HETEROCYCLES; HETEROATOMS; HETEROCYCLES; HYDROXY GROUPS; OXIDATIVE CYCLIZATION; PYRROLIDINES; STARTING MATERIALS; STEREOSPECIFIC; TETRAHYDRO-FURANS; TOTAL SELECTIVITY;

AMIDES; CATALYSIS; ORGANIC COMPOUNDS; OSMIUM; SULFUR COMPOUNDS;

CYCLIZATION;

FURAN DERIVATIVE; HETEROCYCLIC COMPOUND; OSMIUM; PYRROLIDINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY; CYCLIZATION; OXIDATION REDUCTION REACTION;

CATALYSIS; CYCLIZATION; FURANS; HETEROCYCLIC COMPOUNDS; OSMIUM; OXIDATION-REDUCTION; PYRROLIDINES;

EID: 68349133878     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.200900168     Document Type: Article

References (56)

1. For a review see: a)V. Piccialli, Synthesis 2008, 2585-2607;
2. manganese: b) E. Klein, W. Rojahn, Tetrahedron 1965, 21, 2353-2358;
3. c) J. E. Baldwin, M. J. Crossley, E. M. M. Lehtonen, J. Chem. Soc. Chem. Commun. 1979, 918-920;
4. d) D. M. Walba, M. D. Wand, M. C. Wilkes, J. Am. Chem. Soc. 1979, 101, 4396-4397;
5. e) R. C. D. Brown, J. F. Keily, Angew. Chem. 2001, 113, 4628-4630;
6. Angew. Chem. Int. Ed. 2001, 40, 4496-4498;
7. f) R. C. D. Brown, C. J. Bataille, R. M. Hughes, A. Kenney, T. J. Luker, J. Org. Chem. 2002, 67, 8079-8085;
8. ruthenium: g) P. H. J. Carlsen, T. Katsuki, V. S. Martin, K. B. Sharpless, J. Org. Chem. 1981, 46, 3936-3938;
9. h) L. Albarella, D. Musumeci, D. Sica, Eur. J. Org. Chem. 2001, 997-1003;
10. i) V. Piccialli, N. Cavallo, Tetrahedron Lett. 2001, 42, 4695-4699;
11. j) S. Roth, S. Gohler, H. Cheng, C. B. W Stark, Eur. J. Org. Chem. 2005, 4109-4118;
12. osmium: k) M. de Champdore, M. Lasalvia, V. Piccialli, Tetrahedron Lett. 1998, 39, 9781-9784.
13. T.J. Donohoe, S. Butterworth, Angew. Chem. 2003, 115, 978-981;
14. Angew. Chem. Int. Ed. 2003, 42, 948-951.
15. a) R. M. Kennedy, S. Tang, Tetrahedron Lett. 1992, 33, 3729-3732;
16. b) S. Tang, R. M. Kennedy, Tetrahedron Lett. 1992, 33, 5299-5302.
17. J. S. M. Wai, I. Markó, J. M. Svendsen, M. G. Finn, E. N. Jacobsen, K. B. Sharpless, J. Am. Chem. Soc. 1989, 111, 1123-1125.
18. a) T J. Donohoe, S. Butterworth, Angew. Chem. 2005, 117, 4844-4846;
19. Angew. Chem. Int. Ed. 2005, 44, 4766-4768;
20. for a related chromium-mediated cyclization, see: b) D. M. Walba, G. S. Stoudt, Tetrahedron Lett. 1982, 23, 727-730.
21. cis-Solamin: a) see reference [5a]; cis-sylvaticin: b) T J. Donohoe, R. M. Harris, J. Burrows, J. Parker, J. Am. Chem. Soc. 2006, 128, 13704-13705.
22. M. Z. Hoemann, Z. Michael, K. A. Agrios, J. Aube, Tetrahedron 1997, 53, 11087-11098.
23. P. Grieco, Y. Musaki, D, Boxler, J. Am. Chem. Soc. 1975, 97, 1597-1599.
24. R. D. Hancock, A. E. Martell, Chem. Rev. 1989, 89, 1875-1914.
25. P. Dupau, R. Epple, A. A. Thomas, V. V. Fokin, K. B. Sharpless, Adv. Synth. Catal. 2002, 344, 421-433.
26. a) V. V. Fokin, K. B. Sharpless, Angew. Chem. 2001, 113, 3563-3565;
27. b) M. A. Andersson, R. Epple, V. V. Fokin, K. B. Sharpless, Angew. Chem. 2002, 114, 490-493;
28. Angew. Chem. Int. Ed. 2002, 41, 472-475.
29. T J. Donohoe, G H. Churchill, K. M. P. Wheelhouse (née Gosby), PA. Glossop, Angew. Chem. 2006, 118, 8193-8196;
30. Angew. Chem. Int. Ed. 2006, 45, 8025-8028.
31. J. R. Gage, D. A. Evans, Org. Synth. Coll. Vol. VIII, 1993, 339-443.
32. Rhenium: a) see reference [3];
33. cobalt: b) S. Inoki, T Mukaiyama, Chem. Lett. 1990, 67-70.
34. For reports on the oxidative cyclization of 1,6-dienes using ruthenium, see: a) V. Piccialli, Tetrahedron Lett. 2000, 41, 3731-3733;
35. b) S. Roth, B. W Stark, Angew. Chem. 2006, 118, 6364-6367;
36. Angew. Chem. Int. Ed. 2006, 45, 6218-6221;
37. manganese: c) R. L. Cecil; R. CD. Brown, Tetrahedron Lett. 2004, 45, 7269-7271;
38. R.C.D. Brown, Tetrahedron Lett. 2004, 45, 7269-7271.
39. a) See reference [4];
40. b) K. Muñiz, I. Almodovar, J. Streuff, M. Nieger, Adv. Synth. Catal. 2006, 348, 1831-1835.
41. Data were collected at low temperature using an Enraf-Nonius KCCD diffractometer [Z. Otwinowski, W Minor, Processing of X-ray Diffraction Data Collected in Oscillation Mode, In Methods Enzymol, Vol. 276 (Eds.: C W Carter, R. M. Sweet), Academic Press, 1997].
42. The crystal structures were solved using SIR92 [A. Altomare, G. Cascarano, C Giacovazzo, A. Guagliardi, M. C Burla, G. Polidori, M. Camalli, J. Appl. Crystallogr. 1994, 27, 435.]
43. and refined using the CRYSTALS software suite [P. W Betteridge, J. R. Carruthers, R. I. Cooper, K. Prout, D. J. Watkin, J. Appl. Crystallogr. 2003, 36, 1487], as per the CIF Crystallographic data (excluding structure factors) for compound 67 have been deposited with the Cambridge Crystallographic Data Centre (CCDC 730223) and copies of these data can be obtained free of charge via www.ccdc.cam.ac.uk/data-request/cif.
44. For examples of pyrrolidine synthesis using catalysis, see: a) C V. Galliford, M. A. Beenen, S. T Nguyen, K. A. Scheidt, Org. Lett. 2003, 5, 3487-3490;
45. b) Q. Yang, J. E. Ney, J. P. Wolfe, Org. Lett. 2005, 7, 2575-2578;
46. c) C Welter, A. Dahnz, B. Brunner, S. Streiff, P. Dübon, G. Helmchen, Org. Lett. 2005, 7, 1239-1242;
47. d) F A. Davis, H. Xu, Y Wu, J. Zhang, Org. Lett. 2006, 8, 2273 -2276.
48. For examples of pyrrolidines in natural products, see: a) J. W Daly, T.F. Spande, H. M. Garraffo, J. Nat. Prod. 2005, 68, 1556-1575;
49. b) N. Asano, R. J. Nash, R. J. Molyneux, G. W Fleet, Tetrahedron: Asymmetry 2000, 11, 1645-1680;
50. J. D. Scott, R. M. Williams, Chem. Rev. 2002, 102, 1669-1730.
51. Aminohydroxylation: a) D. W Patrick, L. K. Truesdale, S. A. Biller, K. B. Sharpless, J. Org. Chem. 1978, 43, 2628-2638;
52. diamination: b) A. O. Chong, K. Oshima, K. B. Sharpless, J. Am. Chem. Soc. 1977, 99, 3420-3426.
53. T J. Donohoe, K. M. P. Wheelhouse (née Gosby), P. J. Lindsay-Scott, P. A. Glossop, I. A. Nash, J. S. Parker, Angew. Chem. 2008, 120, 2914-2917;
54. Angew. Chem. Int. Ed. 2008, 47, 2872-2875.
55. For a related inverse electron-demand cycloaddition, see: L. R. Domingo, Eur. J. Org. Chem. 2000, 2265-2272.
56. M. Schröder, A. J. Neielson, W P. Griffith, J. Chem. Soc. Dalton Trans. 1979, 1607-1611.