Unusual and efficient (Z)-stereoselective Peterson synthesis of 2-diethoxyphosphonyl-1-alkoxy-3-methylpenta-1,3-dienes. Their use in the Diels-Alder reaction

Tetrahedron Letters

Volumn 37, Issue 17, 1996, Pages 2951-2954

  Al Badri, Hashim ^a   About Jaudet, Elie ^a   Collignon, Noël ^a  

^a UNIVERSITÉ ET INSA DE ROUEN   (France)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHONIC ACID DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030001963     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00452-2     Document Type: Article

References (22)

1. Yuan, C.; Yas, J.; Li, S. Phosphorus, sulfur, and Silicon, 1991, 55, 125-131 and Ref. cited.
2. Muller, E.L.; Modro, A.M.; Modro, T. A. Bull. Soc. Chim. Fr. 1994, 131, 959-964 and Ref. cited.
3. Al-Badri, H.; About-Jaudet, E.; Collignon, N. Synthesis, 1994, 1072-1078 and Ref. cited.
4. Al-Badri, H.; About-Jaudet, E.; Combret, J.-C.; Collignon, N. Synthesis, 1995, 1401-1404.
5. Al-Badri, H.; About-Jaudet, E.; Collignon, N. Tetrahedron Lett. 1995, 36, 393-396.
6. Al-Badri, H.; About-Jaudet, E.; Collignon, N. J. Chem. Soc. Perkin Trans. 1, accepted for publication.
7. 31P NMR spectroscopy [δ (THF) ∼ 44 ppm].
8. 1 Moreover, above (transoid / cisoid)-3d mixture was able to be transformed into pure cisoid-3d by heating at 120°C for 4-5 h.
9. 3JpH values of ∼10 Hz were observed for similar dienes of 1-(E)-configuration; see Ref. 4.
10. Bartoldi, G.; Palmieri, G.; Petrini, M.; Bosco, M.; Dalpozzo, R. Tetrahedron, 1990, 46, 1379-1384.
11. Couture, A.; Cornet, H.; Grandclaudon, P. J. Organomet. Chem. 1992, 440, 7-13.
12. Teulade, M.-P.; Savignac, P. J. Organomet. Chem. 1988, 338, 295-303.
13. Zanella, Y.; Berté-Verrando, S.; Dizière, R.; Savignac, P. J. Chem. Soc. Perkin Trans. 1, 1995, 2835-2838.
14. 31P NMR spectroscopy, we were unable to detect any signal corresponding to the adduct, even at -70°C.
15. The predominant formation of the erythro-adduct could result from a chelation control by the phosphonyl group during the addition of 2c to the formate. For a discussion of the Peterson reaction mechanism, see for example : Bassindale, A.R.; Ellis, R.J.; Lau, J.C.-Y.; Taylor, P.G. J. Chem. Soc. Perkin Trans. II, 1986, 593-597 and Ref. cited.
16. 1H NMR spectroscopy. Any NOE effect could not be detected when 3a was subjected to a similar experiment : the transoid conformation was assigned to this structure. For other examples in a related series, see : Brel', V.K.; Komarov, V.Ya.; Ionin, B.I.; Petrov, A.A. Zh. Obshch. Khim. 1983, 53, 66-75.
17. Minami, T.; Chikugo, T.; Hanamoto, T. J. Org. Chem. 1986, 51, 2210-2214 and Ref. cited.
18. Brel', V.K.; Abramkin, E.V.; Martynov, I.V. Izvset. Akad. Nauk SSSR, Ser. Khim. 1989, 2843-2845.
19. Yuan, C.; Li, C. Heteroatom. Chem. 1992, 3, 637-646.
20. 6; 174.8, d (1.8), C=O; 176.0, s, C=O. MS (70 eV) : 421 (M+); 406 (M-15); 391, 376, 243, 187, 91, 77, 29.
21. 3. See, for example : Barluenga, J.; Tomas, M.; Ballesteros, A., Lopez, L.A. Synthesis, 1995, 985-988.
22. For a review on the synthetic applications of alkenylphosphonates, see : Minami, T.; Motoyoshiya, J. Synthesis, 1992, 333-349.