Diastereo- and enantioselective intramolecular [2+2] Photocycloaddition reactions of 3-(ω'-alkenyl)- and 3-(ω'-alkenyloxy)-Substituted 5,6-Dihydro-1H-pyridin-2-Ones

Chemistry - A European Journal

Volumn 16, Issue 14, 2010, Pages 4284-4296

  Albrecht, Dominik ^a   Vogt, Florian ^a   Bach, Thorsten ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

Asymmetric synthesis; Cycloaddition; Enantioselectivity; Hydrogen bonds; Photochemistry

Indexed keywords

[2 + 2] PHOTOCYCLOADDITION; ALKENYL; ASYMMETRIC SYNTHESIS; CHIRAL TEMPLATES; CHLORIDE IONS; CROSS-COUPLINGS; DIASTEREOSELECTIVE; ENANTIOSELECTIVE; NUCLEOPHILIC DISPLACEMENT; OXIDATIVE ELIMINATION; PHOTOCYCLOADDITION; PHOTOCYCLOADDITION REACTION; PRECURSOR COMPOUNDS; QUINOLONES;

AVIATION; CHLORINE COMPOUNDS; ELECTRON TRANSITIONS; ENANTIOSELECTIVITY; HYDROGEN BONDS; IRRADIATION; TOLUENE;

SYNTHESIS (CHEMICAL);

EID: 77950823167     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200902616     Document Type: Article

References (62)

1. Reviews: a) T. Bach in Asymmetrie Synthesis-The Essentials (Eds.: S. Bräse, M. Christmann), Wiley-VCH, Weinheim, 2006, pp. 166-170;
2. b) S. Breitenlechner, P. Selig, T. Bach in Ernst Schering Foundation Symposium Proceedings "Organocatalysis" (Eds.: M. T. Reetz, B. List, S. Jaroch, H. Weinmann), Springer, Berlin, 2008, pp. 255-280;
3. c) C. Müller, T. Bach, Aust. J. Chem. 2008, 61, 557-564.
4. a) T. Bach, H. Bergmann, K. Harms, Angew. Chem. 2000, 112, 2391-2393;
5. Angew. Chem. Int. Ed. 2000, 39, 2302-2304;
6. b) T. Bach, H. Bergmann, J. Am. Chem. Soc. 2000, 122, 11525-11526;
7. c) T. Bach, H. Bergmann, B. Grosch, K. Harms, J. Am. Chem. Soc. 2002, 124, 7982-7990;
8. d) S. Brandes, P. Selig, T. Bach, Synlett 2004, 2588-2590;
9. e) P. Selig, T. Bach, J. Org. Chem. 2006, 71, 5662-5673.
10. a) P. Selig, T. Bach, Angew. Chem. 2008, 120, 5160-5162;
11. Angew. Chem. Int. Ed. 2008, 47, 5082-5084;
12. b) P. Selig, E. Herdtweck, T. Bach, Chem. Eur. J. 2009, 15, 3509-3525.
13. a) H. Bergmann, B. Grosch, S. Sitterberg, T. Bach, J. Org. Chem. 2004, 69, 970-973;
14. b) A. Bauer, T. Bach, Tetrahedron: Asymmetry 2004, 15, 3799-3803.
15. D. Albrecht, B. Basler, T. Bach, J. Org. Chem. 2008, 73, 2345-2356.
16. J. P. Hehn, C. Müller, T. Bach in Handbook of Synthetic Photochemistry (Eds.: A. Albini, M. Fagnoni), Wiley-VCH, Weinheim, 2009, pp. 171-215.
17. D. Albrecht, T. Bach, Synlett 2007, 1557-1560.
18. Y. Torisawa, T. Soe, C. Katoh, Y. Motohashi, A. Nishida, T. Hino, M. Nakagawa, Heterocycles 1998, 47, 655-660.
19. For Sonogashira and Stille cross-coupling reactions, see: a) A. Gagnon, S. J. Danishefsky, Angew. Chem. 2002, 114, 1651-1654;
20. Angew. Chem. Int. Ed. 2002, 41, 1581-1584;
21. b) J. Dijkink, J.-C. Cintrat, W.N. Speckamp, H. Hiemstra, Tetrahedron Lett. 1999, 40, 5919-5922;
22. c) C. D. Cox, T. Siu, S. J. Danishefsky, Angew. Chem. 2003, 115, 5783-5787;
23. Angew. Chem. Int. Ed. 2003, 42, 5625-5629.
24. a) X. Li, P. Huang, J. J. Cui, J. Zhang, C. Tang, Bioorg. Med. Chem. Lett. 2003, 13, 1939-1942;
25. b) T. G. Back, The Chemistry of Organic Selenium and Tellurium Compounds (Ed.: S. Patai), Wiley, New York, 1987, pp. 91-213.
26. C. R. Johnson, J. P. Adams, M. P. Braun, C. B. W. Senanayake, P. M. Wovkulich, M. R. Uskokovic, Tetrahedron Lett. 1992, 33, 917-918.
27. S. Hou, Org. Lett. 2003, 5, 423-425.
28. J. E. Milne, S. L. Buchwald, J. Am. Chem. Soc. 2004, 126, 13028-13032.
29. K. T. Potts, T Rochanapruk, J. Org. Chem. 1995, 60, 3795-3805.
30. D. X Buckley, M. A. McKervey, J. Chem. Soc. Perkin Trans. 1 1985, 2193-2200.
31. A. Bhalla, P. Venugopalan, K. K. Bhasin, S. S. Bari, Tetrahedron 2007, 65, 3195-3204.
32. I. S. Hutchinson, S. A. Matlin, A. Mete, Tetrahedron 2002, 58, 3137-3143.
33. a) M. Ikeda, M. Takahashi, K. Ohno, Y. Tamura, M. Kido, Chem. Pharm. Bull. 1982, 30, 2269-2271;
34. b) F. Toda, H. Miyamoto, K. Takeda, R. Matsugawa, N. Maruyama, J. Org. Chem. 1993, 58, 6208-6211;
35. c) M. X Begley, M. Mellor, G. Pattenden, J. Chem. Soc. Perkin Trans. 1 1983, 1905-1912;
36. d) S.M. Ng, S. J. Bader, M. L. Snapper, J. Am. Chem. Soc. 2006, 128, 7315-7319.
37. a) N.-Y. Fu, S.-H. Chan, H. N. G Wong in The Chemistry of Functional Groups: The Chemistry of Cyclobutanes: The Application of Cyclobutane Derivatives in Organic Synthesis (Eds.: Z. Rappoport, J. F. Liebman), Wiley, New York, 2005, pp. 357-440;
38. b) J. M. Tanko in The Chemistry of Functional Groups: The Chemistry of Cyclobutanes: Rearrangements of Cyclobutanes (Eds.: Z. Rappoport, J. F. Liebman), Wiley, New York, 2005, pp. 497-519;
39. c) W. M. Horspool in The Chemistry of Functional Groups: The Chemistry of Cyclobutanes: Photochemistry of Cyclobutanes: Synthesis and Reactivity (Eds.: Z. Rappoport, J. F. Liebman), Wiley, New York, 2005, pp.715-805;
40. d) J. C. Namyslo, D.E. Kaufmann, Chem. Rev. 2003, 103, 1485-1537;
41. e) E. Lee-Ruff, G. Mladenova, Chem. Rev. 2003, 103, 1449-1483.
42. S. Breitenlechner, T. Bach, Angew. Chem. 2008, 120, 8075-8077;
43. Angew. Chem. Int. Ed. 2008, 47, 7957-7959.
44. We cordially thank Prof Dr. S. Grimme (Universität Münster) for performing the calculation reactions: a) R. Bauernschmitt, R. Ahlrichs, Chem. Phys. Lett. 1996, 256, 454-464;
45. b) F. Furche, R. Ahlridia, A. Sobanski, F. Vögtle, C. Wachsman, E. Weber, S. Grimme, J. Am. Chem. Soc. 2000, 122, 1717-1724.
46. a) K. A. Connors, Binding Constants - The Measurement of Molecular Complex Stability, Wiley, New York 1.987;
47. b) C. S. Wilcox, in Frontiers in Supramolecular Organic Chemistry and Photochemistry (Eds.: H.-J. Schneider, H. Dürr), VCH, Weinheim 1991, pp. 123-143.
48. a) J. D. Trevor, J. Rebek, J. Am. Chem. Soc. 2006, 128, 4500-4501;
49. b) D. S. Kemp, K. S. Petrakis, J. Org. Chem. 1981, 46, 5140-5143.
50. M. Kajino, Y. Shibouta, K. Nishikawa, K. Meguro, Chem. Pharm. Bull. 1991, 39, 2896-2905.
51. T. Curtius, J. Prakt. Chem. 1895, 52, 243-271.
52. I. Huc, J. Rebek, Tetrahedron Lett. 1.994, 35, 1035-1038.
53. T. Bach, H. Bergmann, B. Grosch, K. Harms, E. Herdtweck, Synthesis 2001, 1395-1405.
54. Examples of dipole/dipole repulsion as a conformational control element in stereoselective reactions: a) S. Masamune, W. Choy, F. A. J. Kerdersky, B. Imperali, J. Am. Chem. Soc. 1981, 103, 1566-1568;
55. b) D. A. Evans, J. Bartroli, T. L. Shih, J. Am. Chem. Soc. 1981, 103, 2127-2129;
56. c) C. M. Lee, W. D. Kumler, J. Am. Chem. Soc. 1961, 83, 4593-4596;
57. d) D. A. Evans, M. J. Dart, J. L. Duffy, M. G. Yang, J. Am. Chem. Soc. 1996, 118, 4322-4343;
58. e) L. E. Overman, E. A. Peterson, Angew. Chem. 2003, 115, 2629-2632;
59. Angew. Chem. Int. Ed. 2003, 42, 2525-2528;
60. f) A. Steven, L. E. Overman, Angew. Chem. 2007, 119, 5584-5605;
61. Angew. Chem. Int. Ed. 2007, 46, 5488-5508;
62. g) G. K. Friestad, A. K. Mathies, Tetrahedron 2007, 63, 9373-9381.