DBU-MeOH promoted one-pot stereoselective γ-functionalization of 1,3- dicarbonyls: Reactivity of β-ketoamides towards α,β-unsaturated aldehydes

Synlett

Volumn , Issue 12, 1999, Pages 1951-1953

  Charonnet, Emmanuelle ^a   Filippini, Marie Hélène ^a   Rodriguez, Jean ^a  

^a UMR au CNRS 6516   (France)

Author keywords

ketoamides, , unsaturated aldehydes; aldol dehydration sequence; allylidenation

Indexed keywords

ALDEHYDE; AMIDE; CARBONYL DERIVATIVE; KETONE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; STEREOCHEMISTRY; STEREOISOMERISM;

EID: 0032738885     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2974     Document Type: Article

References (28)

1. Filippini, M.-H; Faure, R.; Rodriguez, J. J. Org. Chem. 1995, 60, 6872-6882; Filippini, M.-H; Rodriguez, J. J. Org. Chem. 1997, 62, 3034-3035; for a recent account, see: Rodriguez, J. Synlett 1999, 505-518.
2. Filippini, M.-H; Faure, R.; Rodriguez, J. J. Org. Chem. 1995, 60, 6872-6882; Filippini, M.-H; Rodriguez, J. J. Org. Chem. 1997, 62, 3034-3035; for a recent account, see: Rodriguez, J. Synlett 1999, 505-518.
3. Filippini, M.-H; Faure, R.; Rodriguez, J. J. Org. Chem. 1995, 60, 6872-6882; Filippini, M.-H; Rodriguez, J. J. Org. Chem. 1997, 62, 3034-3035; for a recent account, see: Rodriguez, J. Synlett 1999, 505-518.
4. Filippini, M.-H.; Rodriguez, J. J. Chem. Soc., Chem. Commun. 1995, 33-34.
5. For an efficient preparation from the corresponding ketoesters, see: Cossy, J.; Thellend, A. Synthesis 1989, 753-755.
6. Computer-assisted structural search on REACS or Beilstein databases gave no answer. See also: Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; pergamon Press: Oxford, 1991; Vol.3. Chapter 1.1 and Vol. 2, Chapters 1.6 and 3.6.
7. a.
8. Moya, P.; Cantin, A.; Castillo, M.-A.; Primo, J.; Miranda, M. A., Primo-Yufera, E. J. Org. Chem. 1998, 63, 8530-8535.
9. Hoffman, R. V.; Huizenga, D. J. J. Org. Chem. 1991, 56, 6435-6439.
10. DeShong, P.; Lowmaster, N. E.; Baralt, O. J. Org. Chem. 1983, 48, 1149-1150.
11. Schlessinger, R. H.; Bebernitz, G. R.; Lin, P. J. Am. Chem. Soc. 1985, 107, 1777-1778.
12. Cossy, J.; Leblanc, C. Tetrahedron Lett. 1989, 31, 4531-4534; Cossy, J.; Thellend, A. Tetrahedron Lett. 1990, 31, 1427-1428; Schultz, Holoboski, M. A. Tetrahedron Lett. 1993, 34, 3021-3024; Meyer, C.; Piva, O.; Pete, J.-P. Tetrahedron Lett. 1996, 37, 5885-5888.
13. Cossy, J.; Leblanc, C. Tetrahedron Lett. 1989, 31, 4531-4534; Cossy, J.; Thellend, A. Tetrahedron Lett. 1990, 31, 1427-1428; Schultz, Holoboski, M. A. Tetrahedron Lett. 1993, 34, 3021-3024; Meyer, C.; Piva, O.; Pete, J.-P. Tetrahedron Lett. 1996, 37, 5885-5888.
14. Cossy, J.; Leblanc, C. Tetrahedron Lett. 1989, 31, 4531-4534; Cossy, J.; Thellend, A. Tetrahedron Lett. 1990, 31, 1427-1428; Schultz, Holoboski, M. A. Tetrahedron Lett. 1993, 34, 3021-3024; Meyer, C.; Piva, O.; Pete, J.-P. Tetrahedron Lett. 1996, 37, 5885-5888.
15. Cossy, J.; Leblanc, C. Tetrahedron Lett. 1989, 31, 4531-4534; Cossy, J.; Thellend, A. Tetrahedron Lett. 1990, 31, 1427-1428; Schultz, Holoboski, M. A. Tetrahedron Lett. 1993, 34, 3021-3024; Meyer, C.; Piva, O.; Pete, J.-P. Tetrahedron Lett. 1996, 37, 5885-5888.
16. Snider, B. B.; Zhang, Q. Tetrahedron Lett. 1992, 33, 5921-5924.
17. Babudri, F.; Ciminale, F.; Di Nunno, L.; Florio, S. Tetrahedron 1982, 38, 557-561.
18. 3: C, 73.3; H, 6.80; N, 4.50. Found: C, 73.31; H, 6.80; N, 4.57.
19. For some synthetic transformations involving related unsaturated cyclic ketones, see: Fuhr, K. F. J. Org. Chem. 1978, 43, 4248-4250. Deli, J.; Lorand, T.; Szabo, D.; Földesi, A. Pharmazi 1984, 39, 539-540. Iwasaki, G.; Sano, M.; Sodeoka, M.; Yoshida, K.; Shibasaki, M. J. Org. Chem. 1988, 53, 4864-4867. Tyndall, D. V.; Al Nakib, T.; Meegan, M. J. Tetrahedron Lett. 1988, 29, 2703-2706. Abdulla, R. F.; Koch, K.; Smitrovich, J. H. Tetrahedron Lett. 1994, 35, 1137-1140.
20. For some synthetic transformations involving related unsaturated cyclic ketones, see: Fuhr, K. F. J. Org. Chem. 1978, 43, 4248-4250. Deli, J.; Lorand, T.; Szabo, D.; Földesi, A. Pharmazi 1984, 39, 539-540. Iwasaki, G.; Sano, M.; Sodeoka, M.; Yoshida, K.; Shibasaki, M. J. Org. Chem. 1988, 53, 4864-4867. Tyndall, D. V.; Al Nakib, T.; Meegan, M. J. Tetrahedron Lett. 1988, 29, 2703-2706. Abdulla, R. F.; Koch, K.; Smitrovich, J. H. Tetrahedron Lett. 1994, 35, 1137-1140.
21. For some synthetic transformations involving related unsaturated cyclic ketones, see: Fuhr, K. F. J. Org. Chem. 1978, 43, 4248-4250. Deli, J.; Lorand, T.; Szabo, D.; Földesi, A. Pharmazi 1984, 39, 539-540. Iwasaki, G.; Sano, M.; Sodeoka, M.; Yoshida, K.; Shibasaki, M. J. Org. Chem. 1988, 53, 4864-4867. Tyndall, D. V.; Al Nakib, T.; Meegan, M. J. Tetrahedron Lett. 1988, 29, 2703-2706. Abdulla, R. F.; Koch, K.; Smitrovich, J. H. Tetrahedron Lett. 1994, 35, 1137-1140.
22. For some synthetic transformations involving related unsaturated cyclic ketones, see: Fuhr, K. F. J. Org. Chem. 1978, 43, 4248-4250. Deli, J.; Lorand, T.; Szabo, D.; Földesi, A. Pharmazi 1984, 39, 539-540. Iwasaki, G.; Sano, M.; Sodeoka, M.; Yoshida, K.; Shibasaki, M. J. Org. Chem. 1988, 53, 4864-4867. Tyndall, D. V.; Al Nakib, T.; Meegan, M. J. Tetrahedron Lett. 1988, 29, 2703-2706. Abdulla, R. F.; Koch, K.; Smitrovich, J. H. Tetrahedron Lett. 1994, 35, 1137-1140.
23. For some synthetic transformations involving related unsaturated cyclic ketones, see: Fuhr, K. F. J. Org. Chem. 1978, 43, 4248-4250. Deli, J.; Lorand, T.; Szabo, D.; Földesi, A. Pharmazi 1984, 39, 539-540. Iwasaki, G.; Sano, M.; Sodeoka, M.; Yoshida, K.; Shibasaki, M. J. Org. Chem. 1988, 53, 4864-4867. Tyndall, D. V.; Al Nakib, T.; Meegan, M. J. Tetrahedron Lett. 1988, 29, 2703-2706. Abdulla, R. F.; Koch, K.; Smitrovich, J. H. Tetrahedron Lett. 1994, 35, 1137-1140.
24. 17
25. Identified by analysis and comparison of their spectral data with previous work, including homo-and heteronuclear correlation experiments, see reference 2. The E, E configuration is evidenced by the high coupling constants found for the protons on the exocyclic diene unit characteristic of 1,2-trans arrangement; typically between 10 and 16 Hz (see for example 3b, ref 12)
26. Cossy, J.; Bouzide, A. Tetrahedron 1997, 53, 5775-5784. Cossy, J.; Bouzide, A.; Pfau, M. J. Org. Chem. 1997, 62, 7106-7113.
27. Cossy, J.; Bouzide, A. Tetrahedron 1997, 53, 5775-5784. Cossy, J.; Bouzide, A.; Pfau, M. J. Org. Chem. 1997, 62, 7106-7113.
28. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923-2925.