Synthesis of enantiomerically pure bicycle[4.2.0]octanes by Cu-catalyzed [2+2] photocycloaddition and enantiotopos-differentiating ring opening

Angewandte Chemie - International Edition

Volumn 45, Issue 33, 2006, Pages 5541-5543

  Braun, Ingbert ^a   Rudroff, Florian ^b   Mihovilovic, Marko D ^b   Bach, Thorsten ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

^b VIENNA UNIVERSITY OF TECHNOLOGY   (Austria)

Author keywords

Asymmetric synthesis; Cycloaddition; Enantioselectivity; Lactones; Oxidation

Indexed keywords

ASYMMETRIC SYNTHESIS; CYCLOADDITION; ENANTIOSELECTIVITY; LACTONES;

ADDITION REACTIONS; OXIDATION; PHOTOCHEMICAL REACTIONS; REACTION KINETICS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

PARAFFINS;

COPPER; OCTANE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

CATALYSIS; COPPER; MOLECULAR STRUCTURE; OCTANES;

EID: 33748655417     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200600946     Document Type: Article

References (55)

1. a) M. Cueto, L. D'Croz, J. L. Mate, A. San-Martin, J. Darias, Org. Lett. 2005, 7, 415-418;
2. b) S. N. Fedorov, O. S. Radchenko, L. K. Shubina, A. I. Kalinovsky, A. V. Gerasimenko, D. Y. Popov, V. A. Stonik, J. Am. Chem. Soc. 2001, 123, 504-505;
3. c) M. Clericuzio, M. Mella, L. Toma, P. V. Finzi, G. Vidari, Eur. J. Org. Chem. 2002, 988-994;
4. d) V. U. Ahmad, A. R. Jassbi, J. Nat. Prod. 1999, 62, 1016-1018;
5. e) T. V. Hansen, Y. Stenstrom in Organic Synthesis: Theory and Applications, Vol. 5 (Ed.: T. Hudlicky), Elsevier, Oxford, 2001, pp. 1-38.
6. Reviews: a) E. Lee-Ruff, G. Mladenova, Chem. Rev. 2003, 103, 1449-1483;
7. b) H. N. C. Wong, P. Margaretha, E. Lee-Ruff, H. Butenschön, G. Mann, H. M. Muchall, L. Fitjer, G. Haufe, Y. Stenstrom, L. K. Syders in Methoden der Organischen Chemie (Houben-Weyl) 4th ed., Vol. E 7e (Ed.: A. de Meijere), Thieme, Stuttgart, 1997, pp. 29-434.
8. Reviews: a) P. Margaretha in Molecular and Supramolecular Photochemistry: Synthetic Organic Photochemistry, Vol. 12 (Eds.: A. G. Griesbeck, J. Mattay), Dekker, New York, 2005, pp. 211-237;
9. b) D. I. Schuster in CRC Handbook of Photochemistry and Photobiology, 2nd ed. (Eds.: W. M. Horspool, F. Lenci), CRC, Boca Raton, FL, 2004, pp. 72.1-24;
10. c) T. Bach, Synthesis 1998, 683-703;
11. d) S. A. Fleming, C. L. Bradford, J. J. Gao in Molecular and Supramolecular Photochemistry: Synthetic Organic Photochemistry, Vol. 1 (Eds.: V. Ramamurthy, K. S. Schanze), Dekker, New York, 1997, pp. 187-243;
12. e) J.-P. Pete, Adv. Photochem. 1996, 21, 135-216;
13. f) J. Mattay, R. Conrads, R. Hoffmann in Methoden der Organischen Chemie (Houben-Weyl) 4th ed., Vol. E 21c (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart, 1995, pp. 3085-3132;
14. g) M. T. Crimmins, T. L. Reinhold, Org. React. 1993, 44, 297-583;
15. h) S. W. Baldwin, Org. Photochem. 1981, 5, 123-225.
16. Examples: a) E. Garcia-Exposito, A. Alvarez-Larena, V. Branchadell, R. M. Ortuno, J. Org. Chem. 2004, 69, 1120-1125;
17. b) A. B. Smith III, N. Kanoh, H. Ishiyama, N. Minakawa, J. D. Rainier, R. A. Hartz, Y. S. Cho, H. F. Cui, W. H. Moser, J. Am. Chem. Soc. 2003, 125, 8228-8237;
18. c) G. Mehta, J. Nandakumar, Tetrahedron Lett. 2001, 42, 7667-7670;
19. d) J. E. Resek, A. I. Meyers, Synlett 1995, 145-146;
20. e) A. Abad, M. Arno, M. L. Marin, R. J. Zaragoza, J. Chem. Soc. Perkin Trans. 1 1993, 1861-1867.
21. Reviews: a) G. Salomon, Tetrahedron 1983, 39, 485-575;
22. b) P. Margaretha in Methoden der Organischen Chemie (Houben-Weyl) 4th ed., Vol. E 17e (Ed.: A. de Meijere), Thieme, Stuttgart 1997, pp. 159-162;
23. c) S. Ghosh in CRC Handbook of Photochemistry and Photobiology, 2nd ed. (Eds.: W. M. Horspool, F. Lenci), CRC, Boca Raton, FL, 2004, pp. 18.1-24.
24. Structural investigations: a) T. Nickel, K.-R. Pörschke, R. Goddard, C. Krüger, Inorg. Chem. 1992, 31, 4428-4430;
25. b) P. H. M. Budzelaar, P. J. J. A. Timmermans, A. Mackor, A. L. Spek, A. J. M. Duisenberg, Acta Crystallogr. Sect. C 1987, 43, 2298-2300.
26. Reviews: a) C. Bolm, C. Palazzi, O. Beckmann in Transition Metals for Organic Synthesis, 2nd ed., Vol. 2 (Eds.: M. Beller, C. Bolm), Wiley-VCH, Weinheim, 2004, pp. 267-274;
27. b) M. D. Mihovilovic, F. Rudroff, B. Groetzl, Curr. Org. Chem. 2004, 8, 1057-1069.
28. Prepared from anti-norbornenol (P. R. Story, J. Org. Chem. 1961, 26, 287-290)
29. after TBDMS protection (E. J. Corey, A. Venkateswarlu, J. Am. Chem. Soc. 1972, 94, 6190-6191)
30. and ring-opening metathesis (P. Schwab, R. H. Grubbs, J. W. Ziller, J. Am. Chem. Soc. 1996, 118, 100-110).
31. +: calcd 252.1909, found 252.1906.
32. a) T. Bach, C. Krüger, K. Harms, Synthesis 2000, 305-320;
33. b) T. Bach, A. Spiegel, Eur. J. Org. Chem. 2002, 645-654;
34. c) T. Bach, A. Spiegel, Synlett 2002, 1305-1307.
35. K. Langer, J. Mattay, A. Heidbreder, M. Möller, Liebigs Ann. Chem. 1992, 257-260.
36. a) C. Bolm, G. Schlingloff, K. Weickhardt, Angew. Chem. 1994, 106, 1944-1946;
37. Angew. Chem. Int. Ed. Engl. 1994, 33, 1848-1849;
38. b) C. Bolm, G. Schlingloff, F. Bienewald, J. Mol. Catal. A 1997, 117, 347-350.
39. 2): calcd 152.0837, found 152.0835.
40. Reviews: a) N. M. Kamerbeek, D. B. Janssen, W. J. H. van Berkel, M. W. Fraaije, Adv. Synth. Catal. 2003, 345, 667-678;
41. b) M. D. Mihovilovic, B. Müller, P. Stanetty, Eur. J. Org. Chem. 2002, 3711-3730;
42. c) J. D. Stewart, Curr. Org. Chem. 1998, 2, 195-216;
43. d) S. M. Roberts, P. W. H. Wan, J. Mol. Catal. B: Enzym. 1998, 4, 111-136.
44. M. D. Mihovilovic, F. Rudroff, B. Grötzl, P. Kapitan, R. Snajdrova, J. Rydz, R. Mach, Angew. Chem. 2005, 117, 3675-3679;
45. Angew. Chem. Int. Ed. 2005, 44, 3609-3613.
46. Possible optimization: a) M. Bocola, F. Schulz, F. Leca, A. Vogel, M. W. Fraaije, M. T. Reetz, Adv. Synth. Catal. 2005, 347, 979-986;
47. b) M. T. Reetz, B. Brunner, T. Schneider, F. Schulz, C. M. Clouthier, M. M. Kayser, Angew. Chem. 2004, 116, 4167-4170;
48. Angew. Chem. Int. Ed. 2004, 43, 4075-4078.
49. For details of recombinant expression systems, see a) M. G. Bramucci, P. C. Brzostowicz, K. N. Kostichka, V. Nagarajan, P. E. Rouviere, S. M. Thomas, PCT Int. Appl., WO 2003020890, 2003; Chem. Abstr. 2003, 138, 233997;
50. b) P. C. Brzostowicz, K. L. Gibson, S. M. Thomas, M. S. Blasko, P. E. Rouviere, J. Bacteriol. 2000, 182, 4241-4248;
51. c) H. Iwaki, Y. Hasegawa, P. C. K. Lau, S. Wang, M. M. Kayser, Appl. Environ. Microbiol. 2002, 68, 5681-5684.
52. a) J. A. Dale, H. S. Mosher, J. Am. Chem. Soc. 1973, 95, 512-519;
53. b) I. Ohtani, T. Kusumi, Y. Kashman, H. Kakisawa, J. Am. Chem. Soc. 1991, 113, 4092-4096.
54. Examples: a) K. Sahasrabudhe, V. Gracias, K. Furness, B. T. Smith, C. E. Katz, D. S. Reddy, J. Aube, J. Am. Chem. Soc. 2003, 125, 7914-7922;
55. b) G. Mehta, D. S. Reddy, Synlett 1997, 612-614.