Carbohydroxypalladation reactions in aqueous medium: An efficient route to 3-(1-Hydroxyaryl)tetrahydrofurans

Tetrahedron Letters

Volumn 38, Issue 50, 1997, Pages 8695-8698

  Galland, Jean Christophe ^a   Savignac, Monique ^a   Genêt, Jean Pierre ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

TETRAHYDROFURAN DERIVATIVE;

ARTICLE; CATALYSIS; CHIRALITY; CYCLIZATION; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS;

EID: 0030732623     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10337-9     Document Type: Article

References (26)

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2. b) Malleron, J.L.; Fiaud, J.C.; Legros, J.Y. « Handbook of Palladium Catalyzed Organic Reactions. », Academic Press, Harcourt Brace & Company publishers, 1997.
3. a) Review: Trost, B.M., Acc. Chem. Res. 1990, 23, 34.
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5. c) Trost, B.M.; Shi, Y. J. Am. Chem. Soc. 1993, 115, 9421-9438.
6. d) Oh, C.H.; Rhim, C.Y.; Kang, J.H.; Kim, A.; Park, B.S.; Seo, Y. Tetrahedron Lett. 1996, 37, 8875-8878.
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11. Miura, K.; Funatsu, M.; Saito, H.; Ito, H.; Hosomi, A. Tetrahedron Lett. 1996, 37, 9059-9062 and references cited therein.
12. Goeke, A.; Sawamura, M.; Kuwano, R.; Ito, Y. Angew. Chem. Int. Ed. Engl. 1996, 35, 662-663. (R,R)-(S,S)-TRAP = (R,R)-2,2"-Bis[(S)-1-(diarylphosphanyl)ethyl]-1,1"-biferrocene.
13. Amatore, C.; Blart, E.; Genêt, J.P.; Jutand, A.; Lemaire-Audoire, S.; Savignac, M. J. Org. Chem., 1995, 60, 6829-6839.
14. @ TPPTS : (m.sufonated triphenylphosphine).
15. a) Genêt, J.P.; Blart, E.; Savignac, M. Synlett, 1992, 715-717.
16. b) Genêt, J.P.; Blart, E.; Savignac, M.; Paris, J.M. Tetrahedron Lett., 1993, 34, 4189-1192.
17. c) Lemaire-Audoire, S.; Savignac, M.; Dupuis, C.; Genêt, J.P. Tetrahedron Lett., 1996, 37, 2003-2006.
18. a) Genêt, J.P.; Blart, E.; Savignac, M.; Lemeune, S.; Lemaire-Audoire, S.; Paris, J.M., Bernard, J.M. Tetrahedron, 1994, 50, 497.
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21. 1H NMR spectrum confirmed the presence of a unique diastereoisomer.
22. 4 and concentrated in vacuo. The crude product was purified by flash-chromatography on Florisil®.
23. +.
24. An alternative mechanism could be a « Wacker-type » cyclization process as depicted below: (equation presented)
25. 2-palladium complex has already been observed by Wang and co-workers in the insertion of norbornadiene into the aryl-palladium bond See: Li, C.; Cheng, C.; Liao, F.; Wang, S. J. Chem. Soc., Chem. Commun., 1991, 710-712.
26. The diastereoselective transfer of a deuterium atom has already been evidenced similarly by Trost and co-workers in the reductive cyclizations of 1,6-and 1,7-enynes: Trost, B.M.; Rise, F. J. Am. Chem. Soc., 1987, 109, 3161-3163.