Synthesis of ethyl (13E)-trifluoromethylretinoate and its analogues by palladium-catalysed cross-coupling

Tetrahedron Letters

Volumn 40, Issue 16, 1999, Pages 3151-3154

  Thibonnet, Jérôme ^a   Prié, Gildas ^a   Abarbri, Mohamed ^a   Duchêne, Alain ^a   Parrain, Jean Luc ^b  

^a UNIVERSITÉ DE TOURS   (France)

^b AIX MARSEILLE UNIVERSITY   (France)

Author keywords

(E) 1,2 bis(tributylstannyl)ethene; Ethyl (13E) trifluoromethylretinoate; Ethyl (Z) 4,4,4 trifluoro 3 iodobut 2 enoate; Sonogashira cross coupling; Stannylmetallation; Stille reactions

Indexed keywords

ETHYL 13 TRIFLUROMETHYLRETINOATE; PALLADIUM COMPLEX; RETINOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOSPECIFICITY; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033574588     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00414-1     Document Type: Article

References (36)

1. a) Welch, J.T. Tetrahedron 1987, 4, 3123-3136 and references cited therein;
2. b) Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications, Filler, R.; Kobayashi, Y.; Yagupolskii, L.; Eds., Elsevier, Amsterdam, 1993.
3. Fluorine in Bioorganic Chemistry, Welch J.T., Eswara-Krishnan S., Eds., Wiley, New York, 1991.
4. a) Francesch, A.; Alvarez, R.; Lopez, S.; De Lera, A.R. J. Org. Chem. 1997, 62, 310-319;
5. b) Groesbeck, M.; Smith, S.O. J. Org. Chem. 1997, 62, 3638-3641.
6. Fluorine-containing Aminoacids, Synthesis and Properties, Kukhar VP, Soloshonok Va, Eds., Wiley, New York, 1995.
7. Bensadat, A.; Félix, C.; Laurent, A.; Laurent, E.; Faure, R.; Thomas, T. Bull. Soc. Chim. Fr. 1996, 133, 509-514.
8. Poulter, C.D.; Wiggins, P.L.; Plummer, T.L. J. Org. Chem. 1981, 46, 1532-1538.
9. Welch, S.C.; Gruber, J.M. J. Org. Chem. 1982, 47, 385-389.
10. a) Siddal, J.B.; Biskup, M.; Fried, J.H. J. Am. Chem. Soc. 1969, 91, 1853-1854;
11. b) Camps, F.; Canela, R.; Coll, J.; Messeguer, A.; Roca, A. Tetrahedron 1978, 34, 2179-2182.
12. a) Francesch, A.; Alvarez, R.; Lopez, S.; De Lera, A.R. J. Org. Chem. 1997, 62, 310-319;
13. b) Groesbeck, M. Smith, S.O. J. Org. Chem. 1997, 62, 3638-3641.
14. a) Gärtner, D.; Oesterhelt, D.; Towner, P.; Hopf, H.; Erst, L. J. Am. Chem. Soc. 1981, 103, 7642-7643;
15. b) Asato, A.E.; Mead, D.; Denny, M.; Bopp, T.T.; Liu, R.S.H. J. Am. Chem. Soc. 1982, 104, 4979-4981;
16. c) Mead, D.; Loh, R.; Kawagoe, K.I.; Kobayashi, N.; Oshima, T.; Kobayashi, Y. Tetrahedron Lett. 1985, 26, 2877-2880;
17. e) Hanzawa, Y.; Yamada, A.; Kobayashi, Y. Tetrahedron Lett. 1985, 26, 2881-2884;
18. f) Mead, D.; Asato, A.E.; Denny, M.; Liu, R.S.H.; Hanzawa, Y.; Taguchi, T.; Yamada, A.; Kobayashi, N.; Hosoda, A.; Kobayashi, Y. Tetrahedron Lett. 1987, 28, 259-262 and references cited therein.
19. Prié, G., Thibonnet, J.; Abarbri, M.; Duchêne, A.; Parrain, J.-L. Synlett 1998, 839-840.
20. Qing, F.L.; Zhang, Y. Tetrahedron Lett. 1997, 38, 6729-6732.
21. For assignment of Z configuration see: a) Camps, F.; Canela, R.; Coll, J.; Messeguer, A.; Roca, A. Tetrahedron 1978, 34, 2179-2182;
22. b) Bégué, J -P.; Bonnet-Delpon, D.; Mesureur, D.; Ourévitch, M. Magn. Reson. Chem. 1991, 29, 675-678
23. c) Tamura, K.; Ishihara, T.; Yamanaka, H. J. Fluorine Chem. 1994, 68, 25-31;
24. C-F coupling constants for carbon 2 of compounds 3 and 5a-d are greater than 5.1 Hz. This strongly supports the Z -configuration of the double bond.
25. Thibonnet, J.; Abarbri, M.; Parrain, J.-L.; Duchêne, A. Synlett 1997, 771-772 and references therein.
26. Ratovelomanana, V.; Linstrumelle, G. Tetrahedron Lett. 1981, 22, 315-318.
27. Kotora, M.; Negishi, E. Tetrahedron Lett. 1998, 38, 9041-9042.
28. a) Negishi, E.-I.; King, A.O.; Klima, W.L. J. Org. Chem. 1980, 45, 2526-2528;
29. b) Negishi, E.-I.; King, A. O.; Tour, J.M. Organic Synthesis; Wiley: New York, 1990; Collect. Vol. VII, p 63.
30. b) Negishi, E.-I.; King, A. O.; Tour, J.M. Organic Synthesis; Wiley: New York, 1990; Collect. Vol. VII, p 63.
31. H-F = 1.3Hz); MS (70 eV): m/z = 366 (M, 18), 351(13), 305(26), 278(11), 277(41), 251(23), 249(10), 237(14), 223(24), 183(10), 171(10), 165(15), 153(13), 152(10), 146(12), 145(16), 143(10), 141(13), 131(14), 129(16), 128(16), 119(14), 115(23), 91(33), 69(71), 55(49), 43(70), 41(100).
32. Lipshutz, B.H.; Ellsworth, E.L.; Dimock, S.H.; Reuter, D.C. Tetrahedron Lett. 1989, 30, 2065-2068.
33. Thibonnet, J.; Abarbri, M.; Duchêne, A.; Parrain, J.-L. Synlett 1999, 141-143. (equation presented)
34. a) Stille, J.K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508;
35. b) Mitchell, T.N. Synthesis 1992, 803.
36. Spectroscopic data of 1 are in agreement with those reported in the literature (ref 10b).