Tandem Michael-Wittig Horner reaction one-pot synthesis of δ-substituted α,β-unsaturated esters

Tetrahedron Letters

Volumn 38, Issue 41, 1997, Pages 7191-7194

  Piva, Olivier ^a   Comesse, Sébastien ^a  

^a UNIVERSITÉ DE REIMS CHAMPAGNE ARDENNE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; CYCLOHEXANE DERIVATIVE; ESTER DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS;

EID: 0030713073     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01729-2     Document Type: Article

References (26)

1. a) Piva, O.; Pete, J.P. Tetrahedron Lett. 1990, 31, 5157-5160.
2. b) Piva, O.; Pete, J.P. Tetrahedron: Asymmetry 1992, 3, 759-768.
3. c) Piva, O. Synlett 1994, 729-731.
4. a) Piva, O.; Caramelle, D. Tetrahedron:Asymmetry 1995, 6, 831-832.
5. b) Piva, O. J. Org. Chem. 1995, 60, 7879-7883.
6. a) Perlmutter, P. Conjugate addition reactions in organic synthesis Pergamon Press: Oxford, 1992.
7. b) Lipshutz, B.H.; Sengupta, S. Org. React. 1992, Vol. 41, pp. 135-631.
8. a) Taylor, R.J.K. Organocopper reagents - A practical approach Oxford University Press: Oxford, 1994.
9. b) Krause, N.; Gerold, A. Angew. Chem. Int. Ed. 1997, 36, 186-204.
10. Maryanoff, B.E.; Reitz, A.B. Chem. Rev. 1989, 89, 863-927.
11. For reviews on other anionic tandem reactions: a) Ho, T.L. Tandem reactions in organic synthesis, Wiley: New-York, 1992, pp. 416-421.
12. b) Waldmann, H. in Organic synthesis highlights II, Ed. Waldmann, H., VCH: Weinheim, 1995, pp. 193-202.
13. c) Tietze, L.F. Chem. Rev. 1996, 96, 115-136.
14. d) Parsons, P.J.; Penkett, C.S.; Shell, A.J. Chem. Rev. 1996, 96, 195-206.
15. Recent exemples of anionic tandem reactions: a) Eriksson, M.; Nilsson, M.; Olsson, T. Synlett 1994, 271-272.
16. b) Callis, D.J.; Thomas, N.F.; Pearson, D.P.J.; Potter, B.V.L. J. Org. Chem. 1996, 61, 4634-4640.
17. c) Yakura, T.; Tsuda, T.; Matsumura, Y.; Yamada, S.; Ikeda, M. Synlett 1996, 985-986.
18. d) Suzuki, K.; Urabe, H.; Sato, F. J. Am. Chem. Soc. 1996, 118, 8729-8730.
19. e) Gunawardena, G.U.; Arif, A.M.; West, F.G. J. Am. Chem. Soc. 1997, 119, 2066-2067.
20. f) Moorhoff, C.M. Tetrahedron 1997, 53, 2241-2252.
21. 13C NMR, IR, MS) and/or elemental analysis.
22. Clive, D.L.J.; Farina, V.; Beaulieu, P.L. J. Org. Chem. 1982, 47, 2572-2582.
23. Tsuda, T.; Hayashi, T.; Satomi, H.; Kawamoto, T.; Saegusa, T. J. Org. Chem. 1986, 51, 537-540.
24. Brown, C.A.; Yamaichi, A. J. Chem. Soc. Chem. Comm. 1979, 100-101.
25. Corey, E.J.; Enders, D. Tetrahedron Lett. 1976, 11-14.
26. Ballini, R.; Petrini, M.; Marcantoni, E.; Rosini, G. Synthesis 1988, 231-233.