Cyclopropyl building blocks for organic synthesis, 139.[1] ethyl cyclopropylidenepyruvate as a novel multifunctional cyclopropyl building block: Facile preparation and basic reaction patterns

Advanced Synthesis and Catalysis

Volumn 349, Issue 7, 2007, Pages 1247-1255

  Bagutski, Viktor ^a   De Meijere, Armin ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

Bicyclic compounds; Cycloadditions; Diels Alder reactions; Methylenecyclopropanes; Michael addition; Spiro compounds

Indexed keywords

EID: 34547148537     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200600617     Document Type: Article

References (49)

1. Part 139 in the series "Cyclopropyl Building Block for Organic Synthesis",
2. for Part 138, see: L. Zhao, B. Yücel, R. P. Scheurich, A. de Meijere, Chem. Asian J. 2007, 273;
3. Part 137: M. Ahmar, M. Knoke, A. de Meijere, B. Cazes, Synthesis 2007, 442.
4. For reviews see: a) A. de Meijere, S. I. Kozhushkov, A. F. Khlebnikov, in: Topics in Current Chemistry, Vol. 207, (Ed.: A. de Meijere), Springer, Berlin, 2000, p 89;
5. b) A. de Meijere, S. I. Kozhushkov, T. Späth, M. von Seebach, S. Löhr, H. Nüske, T. Pohlmann, M. EsSayed, S. Bräse, Pure Appl. Chem. 2000, 72, 1745;
6. c) A. de Meijere, S. I. Kozhushkov, Eur. J. Org. Chem. 2000, 3809.
7. For reviews, see: a) A. Brandi, S. Cicchi, F. M. Cordero, A. Goti, Chem. Rev. 2003, 103, 1213;
8. b) A. de Meijere, S. I. Kozhushkov, L. P. Hadjiarapoglou, in: Topics in Current Chemistry, Vol. 207, (Ed.: A. de Meijere), Springer, Berlin, 2000, p 149;
9. c) A. de Meijere, L. Wessjohann, Synlett 1990, 20.
10. A. de Meijere, A. Leonov, T. Heiner, M. Noltemeyer, M. T. Bes, Eur. J. Org. Chem. 2003, 472.
11. I. Nakamura, T. Nemoto, Y. Yamamoto, A. de Meijere, Angew. Chem. 2006, 118, 5300;
12. Angew. Chem. Int. Ed. 2006, 45, 5176.
13. K. Tokuzaki, Y. Kanemitu, T. Yoshimitsu, H. Nagaoka, Tetrahedron Lett. 2000, 41, 5923.
14. D. Spitzner, G. Sawitzki, J. Chem. Soc., Perkin Trans. 1 1988, 373.
15. G.-A. Cao, K.-F. Cheng, Synth. Commun. 1996, 26, 1525.
16. a) A. de Meijere, I. D. Kuchuk, V. V. Sokolov, T. Labahn, K. Rauch, M. Es-Sayed, T. Krämer, Eur. J. Org. Chem. 2003, 985;
17. b) X. Huang, H. Zhou, W. Chen, J. Org. Chem. 2004, 69, 839.
18. N. F. Osborne, J. Chem. Soc., Perkin Trans. 1 1982, 1435.
19. a) L. Wessjohann, G. McGaffin, A. de Meijere, Synthesis 1989, 359;
20. b) L. Wessjohann, N. Krass, D. Yu, A. de Meijere, Chem. Ber. 1992, 125, 867;
21. c) M. W. Nötzel, T. Labahn, M. Es-Sayed, A. de Meijere, Eur. J. Org. Chem. 2001, 3025;
22. d) M. Tamm, M. Thutewohl, C. B. Ricker, N. T. Bes, A. de Meijere, Eur. J. Org. Chem. 1999, 2017;
23. e) M. W. Nötzel, M. Tamm, T. Labahn, M. Noltemeyer, M. Es-Sayed, A. de Meijere, J. Org. Chem. 2000, 65, 3850;
24. f) M. W. Nötzel, K. Rauch, T. Labahn, A. de Meijere, Org. Lett. 2002, 4, 839.
25. a) J. Salaün, F. Bennani, J.-C. Compain, A. Fadel, J. Ollivier, J. Org. Chem. 1980, 45, 4129;
26. b) D. Spitzner, H. Swoboda, Tetrahedron Lett. 1986, 27, 1281.
27. M. Limbach, S. Dalai, A. de Meijere, Adv. Synth. Catal. 2004, 346, 760.
28. A. Lechevallier, F. Huet, J. M. Conia, Tetrahedron 1983, 39, 3307.
29. a) G. Rousseau, A. Lechevallier, F. Huet, J. M: Conia, Tetrahedron Lett. 1978, 3287;
30. b) A. Stolle, J. Ollivier, P. P. Piras, J. Salaün, A. de Meijere, J. Am. Chem. Soc. 1992, 114, 4051.
31. M. Mauduit, C. Kouklovsky, Y. Langlois, Tetrahedron Lett. 1998, 39, 6857.
32. T. Liese, F. Seyed-Mahdavi, A. de Meijere, Org. Synth. 1990, 69, 148.
33. A. de Meijere, R. R. Kostikov, A. I. Savchenko, S. I. Kozhushkov, Eur. J. Org. Chem. 2004, 3992.
34. The procedure for the preparation of compound 4 was adopted from: T. Imai, S. Nishida, Synthesis 1993, 395.
35. Cyclopropanation of 4 was carried out according to an appropriately modified procedure adopted from: N. Moszner, F. Zeuner, U. K. Fischer, V. Rheinberger, A. de Meijere, V. Bagutski, Macromol. Rapid Commun. 2003, 24, 269.
36. Z. Yang, J. C. Lorenz, Y. Shi, Tetrahedron Lett. 1998, b 39, 8621.
37. D. A. Evans, J. D. Burch, Org. Lett. 2001, 3, 503.
38. R. K. Boeckman, Jr., P. Shao, J. J. Mullins, Org. Synth. Coll. Vol. 10, p 696.
39. L. M. Harwood, Aldrichimica Acta 1985, 18, 25.
40. [7];
41. b)A. de Meijere, S. Teichmann, D. Yu, J. Kopf, M. Oly, N. von Thienen, Tetrahedron 1989, 45, 2957; hydrogen cyanide:
42. c) T. Liese, S. Teichmann, A. de Meijere, Synthesis 1988, 25;
43. organometallics: d) S. Dalai, M. Limbach, L. Zhao, M. Tamm, M. Sevvana, A. de Meijere, Synthesis 2006, 471; nitromethane:
44. e) F. Seyed-Mahdavi, S. Teichmann, A. de Meijere, Tetrahedron Lett. 1986, 27, 6185;
45. [11b].
46. [18]
47. V. Bagutski, N. Moszner, F. Zeuner, U. K. Fischer, A. de Meijere, Adv. Synth. Catal. 2006, 348, 2133.
48. [18]), 1j under similar reaction conditions afforded the respective Michael adduct.
49. R. Lespieau, M. Bourguel, Org. Synth. Coll. Vol. 1, pp. 209.