Photochemistry of α-diketones in carbohydrates: Anomalous norrish typea II photoelimination and norrish-yang photocyclization promoted by the internal carbonyl group

Chemistry - A European Journal

Volumn 20, Issue 9, 2014, Pages 2663-2671

  Alvarez Dorta, Dimitri ^a   Leõn, Elisa I ^a   Kennedy, Alan R ^b   Martín, Angeles ^a   Pérez Martín, Inés ^a   Riesco Fagundo, Concepciõn ^a   Suárez, Ernesto ^a  

^a INSTITUTO DE PRODUCTOS NATURALES Y AGROBIOLOGÍA   (Spain)

^b UNIVERSITY OF STRATHCLYDE   (United Kingdom)

Author keywords

carbohydrates; cyclization; diketones; photochemistry; radicals

Indexed keywords

ATOMS; CARBOHYDRATES; CHEMICAL REACTIONS; CRYSTALLINE MATERIALS; CYCLIZATION; FREE RADICAL REACTIONS; MUSCULOSKELETAL SYSTEM; PHOTOCHEMICAL REACTIONS; PHOTOLYSIS; REGIOSELECTIVITY;

CRYSTALLINE STATE; DIKETONES; HYDROGEN ATOM TRANSFERS (HAT); PHOTOCHEMICAL PROCESS; RADICALS; STEREOELECTRONIC EFFECT; SYNTHETIC YIELDS; TRANSITION STATE;

KETONES;

EID: 84897664103     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201303843     Document Type: Article

References (78)

1. P. J. Wagner, in Synthetic Organic Photochemistry (Molecular and Supramolecular Photochemistry), Vol.a 12 (Eds.:, A.a G. Griesbeck, J. Mattay,), Marcel Dekker, New York, 2005, pp.a 11-39
2. P. Wessig, O. Mühling, in Synthetic Organic Photochemistry (Molecular and Supramolecular Photochemistry), Vol.a 12 (Eds.:, A.a G. Griesbeck, J. Mattay,), Marcel Dekker, New York, 2005, pp.a 41-87
3. P. J. Wagner, P. Klán, in Handbook of Organic Photochemistry and Photobiology, Vol.a 1 (Eds.:, W.a M. Horspool, F. Lenci,), CRC, Boca Raton, 2003, chaptera 52, pp.a 1-31
4. T. Hasegawa, in Handbook of Organic Photochemistry and Photobiology, Vol.a 1 (Eds.:, W.a M. Horspool, F. Lenci,), CRC, Boca Raton, 2003, chaptera 55, pp.a 1-23
5. P. Wessig, in Handbook of Organic Photochemistry and Photobiology, Vol.a 1 (Eds.:, W.a M. Horspool, F. Lenci,), CRC, Boca Raton, 2003, chaptera 57, pp.a 1-20
6. P. J. Wagner, in Handbook of Organic Photochemistry and Photobiology, Vol.a 1 (Eds.:, W.a M. Horspool, F. Lenci,), CRC Press, Boca Raton, 2003, chaptera 58, pp.a 1-70
7. P. J. Wagner, B.-S. Park, in Organic Photochemistry, Vol.a 11 (Ed.:, A. Padwa,), Marcel Dekker, New York, 1991, pp.a 227-365
8. P. J. Wagner, Acc. Chem. Res. 1989, 22, 83-91.
9. D. Álvarez-Dorta, E. I. Leõn, A. R. Kennedy, C. Riesco-Fagundo, E. Suárez, Angew. Chem. 2008, 120, 9049-9051
10. Angew. Chem. Int. Ed. 2008, 47, 8917-8919
11. D. Alvarez-Dorta, E. I. Leõn, A. R. Kennedy, A. Martín, I. Pérez-Martín, C. Riesco-Fagundo, E. Suárez, Chem. Eur. J. 2013, 19, 10312-10333.
12. R. Bishop, J. Chem. Soc. Chem. Commun. 1972, 1288-1289
13. S. Mohr, Tetrahedron Lett. 1980, 21, 593-594. The issue of which of the two carbonyl groups initially abstracts the hydrogen atom in the formation of α-hydroxycyclopentanones by photolysis of α-diketones has been a point of some controversy, see
14. Y. Ogata, K. Takagi, J. Org. Chem. 1974, 39, 1385-1386
15. T. Burkoth, E. Ullman, Tetrahedron Lett. 1970, 11, 145-148
16. R. Bishop, N. K. Hamer, J. Chem. Soc. C 1970, 1193-1197.
17. Modern Aldol Reactions, Vols.a 1, 2 (Ed.:, R. Mahrwald,), Wiley-VCH, Weinheim, 2004
18. E. M. Carreira, A. Fettes, C. Martí, Org. React. 2006, 67, 1-216.
19. W. H. Urry, D. J. Trecker, J. Am. Chem. Soc. 1962, 84, 118-120
20. P. J. Wagner, R. G. Zepp, K.-C. Liu, M. Thomas, T.-J. Lee, N. J. Turro, J. Am. Chem. Soc. 1976, 98, 8125-8134.
21. T. Y. Kim, B. S. Park, Bull. Korean Chem. Soc. 1997, 18, 141-142
22. R. L. Blankespoor, R. L. Dea Jong, R. Dykstra, D. A. Hamstra, D. B. Rozema, D. P. VanMeurs, P. Vink, J. Am. Chem. Soc. 1991, 113, 3507-3513. For general reviews on the captodative effect, see
23. H. G. Viehe, Z. Janousek, B. Merenyi, L. Stella, Acc. Chem. Res. 1985, 18, 148-154
24. L. Stella, J. N. Harvey, in Radicals in Organic Synthesis, Vol.a 1 (Eds.:, P. Renaud, M. Sibi,), Wiley-VCH, Weinheim, 2001, pp.a 298-314.
25. P. J. Wagner, J. Am. Chem. Soc. 1967, 89, 5898-5901
26. R. R. Sauers, S.-Y. Huang, Tetrahedron Lett. 1990, 31, 5709-5712
27. U. Lindemann, G. Reck, D. Wulff-Molder, P. Wessig, Tetrahedron 1998, 54, 2529-2544
28. K. Vishnumurthy, E. Cheung, J. R. Scheffer, C. Scott, Org. Lett. 2002, 4, 1071-1074
29. D. Braga, S. Chen, H. Filson, L. Maini, M. R. Netherton, B. O. Patrick, J. R. Scheffer, C. Scott, W. Xia, J. Am. Chem. Soc. 2004, 126, 3511-3520.
30. Philips master PL electronic lamp 23a W/865.
31. G. A. Adams, C. T. Bishop, J. Am. Chem. Soc. 1956, 78, 2842-2844
32. S. Mukherjee, H. C. Srivastava, J. Am. Chem. Soc. 1955, 77, 422-423.
33. H. Ihmels, J. R. Scheffer, Tetrahedron 1999, 55, 885-907
34. A. Natarajan, T. T. Mague, V. Ramamurthy, J. Am. Chem. Soc. 2005, 127, 3568-3576
35. W. Xia, J. R. Scheffer, M. Botoshansky, M. Kaftory, Org. Lett. 2005, 7, 1315-1318.
36. H6,H7 experimental constants were obtained by iterative simulation of the spectra using DAISY as implemented in TOPSPIN v. 2.1 for Bruker.
37. D. A. Evans, M. C. Kozlowski, C. S. Burgey, D. W. C. MacMillan, J. Am. Chem. Soc. 1997, 119, 7893-7894
38. D. A. Evans, C. S. Burgey, M. C. Kozlowski, S. W. Tregay, J. Am. Chem. Soc. 1999, 121, 686-699
39. K. Juhl, N. Gathergood, K. A. Jorgensen, Chem. Commun. 2000, 2211-2212
40. R. Roers, G. L. Verdine, Tetrahedron Lett. 2001, 42, 3563-3565
41. S. Orlandi, A. Mandoli, D. Pini, P. Salvadori, Angew. Chem. 2001, 113, 2587-2589
42. Angew. Chem. Int. Ed. 2001, 40, 2519-2521
43. P. I. Dalko, L. Moisan, J. Cossy, Angew. Chem. 2002, 114, 647-650
44. Angew. Chem. Int. Ed. 2002, 41, 625-628
45. H. L. vana Lingen, J. K. W. vana dea Mortel, K. F. W. Hekking, F. L. vana Delft, T. Sonke, F. P. J. T. Rutjes, Eur. J. Org. Chem. 2003, 317-324
46. P. Dambruoso, A. Massi, A. Dondoni, Org. Lett. 2005, 7, 4657-4660; For an example of intramolecular carbonyl ene reaction where a pyruvate moiety acts as enophile, see
47. S. Kaden, M. Hiersemann, Synlett 2002, 1999-2002.
48. A. Hense, S. V. Ley, H. M. I. Osborn, D. R. Owen, J.-F. Poisson, S. L. Warriner, K. E. Wesson, J. Chem. Soc. Perkin Trans. 1 1997, 2023-2031
49. H. Liu, R. Nasi, K. Jayakanthan, L. Sim, H. Heipel, D. R. Rose, B. M. Pinto, J. Org. Chem. 2007, 72, 6562-6572; For a review on Ley protectors, see
50. S. V. Ley, D. K. Baeschlin, D. J. Dixon, A. C. Foster, S. J. Ince, H. W. M. Priepke, D. J. Reynolds, Chem. Rev. 2001, 101, 53-80.
51. H.-G. Korth, J. P. Praly, L. Somsák, R. Sustmann, Chem. Ber. 1990, 123, 1155-1160.
52. J. Dupuis, B. Giese, D. Ruegge, H. Fischer, H.-G. Korth, R. Sustmann, Angew. Chem. 1984, 96, 887-888
53. Angew. Chem. Int. Ed. Engl. 1984, 23, 896-898
54. H.-G. Korth, R. Sustmann, J. Dupuis, B. Giese, J. Chem. Soc. Perkin Trans. 2 1986, 1453-1459
55. H.-G. Korth, R. Sustmann, K. S. Gröninger, T. Witzel, B. Giese, J. Chem. Soc. Perkin Trans. 2 1986, 1461-1464
56. H.-G. Korth, R. Sustmann, K. S. Gröninger, M. Leisung, B. Giese, J. Org. Chem. 1988, 53, 4364-4369
57. H.-G. Korth, R. Sustmann, B. Giese, B. Rückert, K. S. Gröninger, Chem. Ber. 1990, 123, 1891-1898; For a review, see
58. J.-P. Praly, Adv. Carbohydr. Chem. Biochem. 2000, 56, 65-151.
59. 1-restricted chair, see Refs.a [16 b, e]. For radical reactivity of restricted and unrestricted D -glucose derivatives at the anomeric center, see:, H. Abe, M. Terauchi, A. Matsuda, S. Shuto, J. Org. Chem. 2003, 68, 7439-7447
60. H. Abe, S. Shuto, A. Matsuda, J. Am. Chem. Soc. 2001, 123, 11870-11882.
61. T. Nishikawa, M. Ishikawa, M. Isobe, Synlett 1999, 123-125
62. M. Isobe, R. Nishizawa, S. Hosokawa, T. Nishikawa, Chem. Commun. 1998, 2665-2676
63. L. F. Tietze, U. Griesbach, I. Schuberth, U. Bothe, A. Marra, A. Dondoni, Chem. Eur. J. 2003, 9, 1296-1302.
64. Y. Landais, J. M. Vincent, Sci. Synth. 2004, 26, 649-730
65. P. S. Bailey, Chem. Rev. 1958, 58, 925-1010
66. T. F. Favino, G. Fronza, C. Fuganti, D. Fuganti, P. Graselli, A. Mele, J. Org. Chem. 1996, 61, 8975-8979
67. L. Re, B. Maurer, G. Ohloff, Helv. Chim. Acta 1973, 56, 1882-1894.
68. M. Schröder, Chem. Rev. 1980, 80, 187-213
69. R. Zibuck, D. Seebach, Helv. Chim. Acta 1988, 71, 237-240.
70. CCDC-893121 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
71. G. Olovsson, J. R. Scheffer, J. Trotter, C.-H. Wu, Tetrahedron Lett. 1997, 38, 6549-6552
72. J. R. Scheffer, C. Scott, in Handbook of Organic Photochemistry and Photobiology, Vol.a 1, 2 nd ed., chaptera 54, (Eds.: W.a M. Horspool, F. Lenci,), CRC, Boca Raton, 2003, pp.a 1-25
73. V. Ramamurthy, K. VenKatosan, Chem. Rev. 1987, 87, 433-481
74. E. Cheung, T. Kang, J. R. Raymond, J. R. Scheffer, J. Trotter, Tetrahedron Lett. 1999, 40, 8729-8732
75. M. Leibovitch, G. Olovsson, J. R. Scheffer, J. Trotter, J. Am. Chem. Soc. 1998, 120, 12755-12769
76. A. D. Gudmundsdottir, T. J. Lewis, L. H. Randall, J. R. Scheffer, S. J. Rettig, J. Trotter, C.-H. Wu, J. Am. Chem. Soc. 1996, 118, 6167-6184
77. P. J. Wagner, R. Pabon, B.-S. Park, A. R. Zand, D. L. Ward, J. Am. Chem. Soc. 1994, 116, 589-596.
78. One example of the formation of an alkoxycarbonyl-cyclobutanol by photolysis of an α-ketoester has been reported, see:, S. Hu, D. C. Neckers, J. Chem. Soc. Perkin Trans. 2 1999, 1771-1778.