Enantioselective access to bicyclo[4.2.0]octanes by a sequence of [2+2] photocycloaddition/reduction/fragmentation

Chemistry - A European Journal

Volumn 19, Issue 38, 2013, Pages 12639-12643

  Yin, Guoyin ^a   Herdtweck, Eberhardt ^a   Bach, Thorsten ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

asymmetric synthesis; cycloaddition; enantioselectivity; photochemistry; reduction

Indexed keywords

[2+2] PHOTOCYCLOADDITION; ASYMMETRIC SYNTHESIS; ENANTIOSELECTIVE; OXYGEN BRIDGE; RING OPENING METATHESIS;

CHEMISTRY; CYCLOADDITION; PHOTOCHEMICAL REACTIONS; REDUCTION; SYNTHESIS (CHEMICAL);

ENANTIOSELECTIVITY;

EID: 84884286213     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201302882     Document Type: Article

References (76)

1. R. Kostikov, M. S. Baird, in Science of Synthesis, Vol.a 48 (Ed.:, H. Hiemstra,), Thieme, Stuttgart, 2009, pp.a 615-646
2. E. Lee-Ruff, G. Mladenova, Chem. Rev. 2003, 103, 1449-1483.
3. H. Ito, M. Hasegawa, Y. Tekenaka, T. Kobayashi, K. Iguchi, J. Am. Chem. Soc. 2004, 126, 4520-4521
4. K. Ishihara, K. Nakano, J. Am. Chem. Soc. 2007, 129, 8930-8931
5. E. Canales, E. J. Corey, J. Am. Chem. Soc. 2007, 129, 12686-12687
6. S. Suárez-Pantiga, C. Hernández-Díaz, E. Rubio, J. M. González, Angew. Chem. 2012, 124, 11720-11723
7. Angew. Chem. Int. Ed. 2012, 51, 11552-11555.
8. C. Müller, A. Bauer, T. Bach, Angew. Chem. 2009, 121, 6767-6769
9. Angew. Chem. Int. Ed. 2009, 48, 6640-6642
10. C. Müller, M. M. Maturi, A. Bauer, M. C. Cuquerella, M. A. Miranda, T. Bach, J. Am. Chem. Soc. 2011, 133, 16689-16697
11. R. Brimioulle, H. Guo, T. Bach, Chem. Eur. J. 2012, 18, 7552-7560.
12. M. Sato, H. Ohuchi, Y. Abe, C. Kaneko, Tetrahedron: Asymmetry 1992, 3, 313-328
13. T. Taniguchi, Y. Goto, K. Ogasawara, Synlett 1997, 707-709
14. T. Nishimura, S. Matsumra, Y. Maeda, S. Uemura, Tetrahedron Lett. 2002, 43, 3037-3039
15. D. Zhao, Z. Zhao, K. Ding, Synlett 2005, 2067-2071
16. I. Braun, F. Rudroff, M. D. Mihovilovic, T. Bach, Angew. Chem. 2006, 118, 5667-5670
17. Angew. Chem. Int. Ed. 2006, 45, 5541-5543
18. I. Braun, F. Rudroff, M. D. Mihovilovic, T. Bach, Synthesis 2007, 24, 3896-3906
19. R. Siedlecka, I. Turowska-Tyrk, Tetrahedron: Asymmetry 2011, 22, 1662-1666
20. M. Luparia, M. T. Oliveira, D. Audisio, F. Frébault, R Goddard, N. Maulide, Angew. Chem. 2011, 123, 12840-12844
21. Angew. Chem. Int. Ed. 2011, 50, 12631-12635.
22. S. Takeda, E. Kurosawa, K. Komiyama, T. Suzuki, Bull. Chem. Soc. Jpn 1990, 63, 3066-3072; Paralemnol
23. H.-C. Huang, Z.-H. Wen, C.-H. Chao, A. F. Ahmed, M. Y. Chiang, Y.-H. Kuo, C.-H. Hsu, J. H. Sheu, Tetrahedron Lett. 2006, 47, 8751-8755; Illudiolone
24. T. C. McMorris, A. Kashinatham, R. Lira, H. Rundgren, P. K. Gantzel, M. J. Kelner, R. Dawe, Phytochemistry 2002, 61, 395-398; Atlanticone D
25. M. Clericuzio, M. Mella, L. Toma, P. V. Finzi, G. Vidari, Eur. J. Org. Chem. 2002, 988-994; Jasonol
26. A. A. Ahmed, A. A. Mahmoud, Tetrahedron 1998, 54, 8141-8152; Echinocidin C
27. Y. Shiono, S. Suzuki, T. Murayama, M. Ikeda, Y. Abe, T. Sassa, Z. Naturforsch. B Chem. Sci. 2005, 60, 449-452.
28. J. P. Hehn, C. Müller, T. Bach, in Handbook of Synthetic Photochemistry (Eds.:, A. Albini, M. Fagnoni,), Wiley-VCH, Weinheim, 2009, 171-215
29. S. A. Fleming, in Molecular and Supramolecular Photochemistry, Vol.a 12 (Eds.:, A.a G. Griesbeck, J. Mattay,), Marcel Dekker, New York, 2005, 141-160
30. P. Margaretha, in Molecular and Supramolecular Photochemistry, Vol.a 12 (Eds.:, A.a G. Griesbeck, J. Mattay,), Marcel Dekker, New York, 2005, 211-237
31. J. P. Pete, in CRC Handbook of Organic Photochemistry and Photobiology, 2nda ed. (Eds.:, W. Horspool, F. Lenci,), CRC Press, Boca Raton, 2004, 71 /1- 71 /14
32. T. Bach, Synthesis 1998, 683-703
33. J.-P. Pete, Adv. Photochem. 1996, 22, 135-216
34. J. Mattay, R. Conrads, R. Hoffmann, in Methoden der Organischen Chemie (Houben-Weyl) 4tea Aufl., (Eds.:, G. Helmchen, R.a W. Hoffmann, J. Mulzer, E. Schaumann,), Thieme, Stuttgart, 1995, Banda E 21 c, 3085- 3132
35. M. T. Crimmins, T. L. Reinhold, Org. React. 1993, 44, 297-588.
36. G. L. Lange, C. Decicco, S. L. Tan, G. Chamberlain, Tetrahedron Lett. 1985, 26, 4707-4710
37. G. L. Lange, C. Decicco, M. Lee, Tetrahedron Lett. 1987, 28, 2833-2836
38. S. Faure, S. Piva-Le-Blanc, C. Bertrand, J.-P. Pete, R. Faure, O. Piva, J. Org. Chem. 2002, 67, 1061-1070
39. K. Tsutsumi, Y. Yanagisawa, A. Furutani, T. Morimoto, K. Kaiuchi, T. Wada, T. Mori, Y. Inoue, Chem. Eur. J. 2010, 16, 7448-7455.
40. R. G. Salomon, Tetrahedron 1983, 39, 485-575
41. P. Margaretha, in Methoden der Organischen Chemie (Houben-Weyl) 4tha ed., (Ed.:, A. Dea Meijere,), Thieme, Stuttgart, 1997, Vola E17e, pp.a 159-162
42. S. Ghosh in CRC, Handbook of Organic Photochemistry and Photobiology, 2nda ed. (Eds.:, W.a M. Horspool, F. Lenci,), CRC, Boca Raton, 2004, 18.1-24.
43. W. K. Anderson, A. S. Milowsky, J. Org. Chem. 1985, 50, 5423-5424
44. E. Utagawa, M. Sekine, K. Seio, J. Org. Chem. 2006, 71, 7668-7677
45. Y. W. Goh, B. R. Pool, J. M. White, J. Org. Chem. 2008, 73, 151-156.
46. P. Schwab, M. B. France, J. W. Ziller, R. H. Grubbs, Angew. Chem. 1995, 107, 2179-2181
47. Angew. Chem. Int. Ed. Engl. 1995, 34, 2039-2041
48. P. Schwab, R. H. Grubbs, J. W. Ziller, J. Am. Chem. Soc. 1996, 118, 100-110
49. T. E. Welhelm, T. R. Belderrain, S. N. Brown, R. H. Grubbs, Organometallics 1997, 16, 3867-3869.
50. H. Tang, N. Yusuff, J. L. Wood, Org.Lett. 2001, 3, 1563-1566
51. D. Banti, M. North, Tetrahedron Lett. 2002, 43, 1561-1564
52. J. D. Winkler, S. M. Asselin, S. Shepard, J. Yuan, Org. Lett. 2004, 6, 3821-3824
53. A. Aljarilla, J. Plumet, Synthesis 2008, 21, 3516-3524.
54. K. Langer, J. Mattay, A. Heidbreder, M. Möller, Liebigs Ann. Chem. 1992, 257-260
55. T. Bach, C. Krüger, K. Harms, Synthesis 2000, 305-320
56. T. Bach, A. Spiegel, Eur. J. Org. Chem. 2002, 645-654.
57. P. Beak, A. Basu, D. J. Gallagher, Y. S. Park, S. Thayumanavan, Acc. Chem. Res. 1996, 29, 552-560
58. P. O'Brien, J. Chem. Soc. Perkin Trans. 1 1998, 1439-1457
59. J.-C. Plaquevent, T. Perrard, D. Cahard, Chem. Eur. J. 2002, 8, 3300-3307
60. G. Wu, M. Huang, Chem. Rev. 2006, 106, 2596-2616
61. J.-C. Kizirian, Chem. Rev. 2008, 108, 140-205.
62. M. Koreeda, K.-Y. Jung, M. Hirota, J. Am. Chem. Soc. 1990, 112, 7413-7414
63. W.-D. Z. Li, K. Wei, Org. Lett. 2004, 6, 1333-1335.
64. K. Matsuki, H. Inoue, A. Ishida, M. Takeda, M. Nakagawa, T. Hino, Chem. Pharm. Bull. 1994, 42, 9-18
65. R. Romagnoli, E. C. Roos, H. Hiemstra, M. J. Moolenaar, W. N. Speckamp, Tetrahedron Lett. 1994, 35, 1087-1090
66. J. Kang, J. W. Lee, J. I. Kim, C. Pyun, Tetrahedron Lett. 1995, 36, 4265-4268
67. M. Ostendorf, R. Romagnoli, I. C. Pereiro, E. C. Roos, M. J. Moolenaar, W. N. Speckamp, H. Hiemstra, Tetrahedron: Asymmetry 1997, 8, 1773-1789
68. M. D. Barker, R. A. Dixon, S. Jones, B. J. Marsh, Tetrahedron 2006, 62, 11663-11669
69. S. Takebayashi, J. M. John, S. H. Bergens, J. Am. Chem. Soc. 2010, 132, 12832-12834.
70. For a combination between [4+4] photocycloaddition and imide desymmetrization, see:, A. C. Spivey, B. I. Andrews, A. D. Brown, C. S. Frampton, Chem. Commun. 1999, 2523-2524.
71. A. Hirao, S. Itsuno, S. Nakahama, N. Yamazaki, J. Chem. Soc. Chem. Commun. 1981, 315-317
72. E. J. Corey, R. K. Bakshi, S. Shibata, J. Am. Chem. Soc. 1987, 109, 5551-5553.
73. K.-H. Chung, H. G. Lee, I.-Y. Choi, J.-R. Choi, J. Org. Chem. 2001, 66, 5937-5939.
74. A. C. Spivey, A. Maddaford, T. Fekner, A. J. Redgrave, C. S. Frampton, J. Chem. Soc. Perkin Trans. 1 2000, 3460-3468.
75. J.-R. Choi, S. Han, J. K. Cha, Tetrahedron Lett. 1991, 32, 6469-6472
76. D. C. Kapeller, F. Hammerschmidt, Chem. Eur. J. 2009, 15, 5729-5739.