Oxidative intramolecular cyclization reactions of cinnamyl ethers mediatedby cerium(IV) ammonium nitrate (CAN): A stereoselective synthesis of3,4-trans-disubstituted tetrahydrofuran derivatives

Arkivoc

Volumn 2003, Issue 8, 2003, Pages 199-210

  Nair, Vijay ^a   Balagopal, Lakshmi ^a   Menon, Rajeev S ^a   Ros, Sindu ^a   Srinivas, R ^b  

^a REGIONAL RESEARCH LABORATORY CSIR   (India)

^b INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Cerium(IV) ammonium nitrate; Cinnamyl ethers; One electron oxidation; Radical cyclization; Tetrahydrofurans

Indexed keywords

(2 METHOXYCINNAMYL)CINNAMYL ETHER; (3,4 DIMETHOXYCINNAMYL)CINNAMYL ETHER; (3,4,5 TRIMETHOXYCINNAMYL)CINNAMYL ETHER; (4 METHOXYCINNAMYL)CINNAMYL ETHER; 2 (2 METHOXYBENZOYL) 2 METHOXY 1 (PROPYN 2 YL 1 OXY)ETHANE; 2 METHOXYCINNAMYL 3 METHYLBUTEN 2 YL ETHER; 2 METHOXYCINNAMYL ETHER; 2 METHOXYCINNAMYLALLYL ETHER; 2 METHOXYCINNAMYLPROPARGYL ETHER; 3 (2 METHOXYBENZOYL) 4 (1 METHOXY 1 METHYL)ETHYLTETRAHYDROFURAN; 3 (2 METHOXYPHENYL) 2,3 DIMETHOXY 1 (BUTEN 2 YL 1 OXY)PROPANE; 3 (2 METHOXYPHENYL) 2,3 DIMETHOXY 1 (PROPEN 2 YL 1 OXY)PROPANE; 3 (2 METHOXYPHENYL) 2,3 DIMETHOXY 1 (PROPYN 2 YL 1 OXY)PROPANE; 3 [METHOXY (2 METHOXYPHENYL)]METHYL 4 (1 METHOXY 1 METHYL)ETHYLTETRAHYDROFURAN; 3 [METHOXY(2 METHOXYPHENYL)]METHYL 4 (METHOXYPHENYL)METHYLTETRAHYDROFURAN; 3 BENZOYL 4 [METHOXY(3,4,5 TRIMETHOXYPHENYL)]METHYLTETRAHYDROFURAN; ALKANE DERIVATIVE; AMMONIUM NITRATE; CERIUM AMMONIUM NITRATE; ETHER DERIVATIVE; TETRAHYDROFURAN DERIVATIVE; UNCLASSIFIED DRUG;

ANAEROBIC METABOLISM; ARTICLE; CYCLIZATION; OXIDATION; STEREOCHEMISTRY;

EID: 3242734729     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (29)

1. (a) Stork, G.; Sher, P. M. J. Am. Chem. Soc. 1983, 105, 6765 and references cited therein.
2. (b) Stork, G.; Baine, N. H. Tetrahedron Lett. 1985, 26, 5927.
3. (a) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon bonds: Pergamon Press, New York, 1986.
4. (b) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. 96, 1996, 177.
5. (c) Bowman, W. R.; Bridge, C. F. Brookes, P.; J. Chem. Soc. Perkin Trans. 1 2000, 1.
6. (d) Beckwith, A. L. J.; Tetrahedron, 1981, 3073.
7. (e) Yet, L. Tetrahedron, 1999, 9349.
8. (f) Gansauer, A.; Bluhm, H. Chem. Rev. 2000, 2771.
9. (a) De Klein, W. Organic Synthesis by Oxidation with Metal Compounds; Mijs, W. J.; de Jonge, C. R. H., Ed.; Plenum: New York, 1986; p. 261.
10. (b) Iqbal, J.; Bhatia, B.; Nayyar, N. K. Chem. Rev. 1994, 94, 519.
11. Molander, G. A. Chem. Rev. 1992, 92, 29.
12. (a) Melikyan, G. G. Synthesis, 1993, 833.
13. (b) Snider, B. B. Chem. Rev. 1996, 96, 339.
14. (c) D'Annibale, A.; Nanni, D.; Troglo, C.; Umani, F. Org. Lett. 2000, 401.
15. (a) Nair, V.; Mathew, J.; Prabhakaran, J. Chem. Soc. Rev. 1997, 127.
16. (b) Nair, V.; Panicker, S. B.; Nair, L. G.; George, T. G.; Augustine, A. Synlett 2002 (accepted).
17. (c) Linker, T.; Linker, U. Angew. Chem. Int. Ed. Engl. 2000, 39, 902.
18. (d) Baciocchi, E.; Casu, A.; Ruzziconi, R. Synlett 1990, 679.
19. (e) Nair, V.; Mathew, J.; Radhakrishnan, K. V. J. Chem. Soc., Perkin Trans. 11996, 1487.
20. (a) Snider, B. B.; Kwon, T. J. Org. Chem. 1990, 55, 4786.
21. (b) Baciocchi, E.; Paolobelli, A. B.; Ruzziconi, R.; Tetrahedron, 1992, 48, 4617.
22. (c) Kim, H. J.; Yoon, U. C.; Jung, Y.; Park, N. S.; Cederstorm, E. M.; Mariano, P. S. J. Org. Chem. 1998, 63, 860.
23. (d) Takemoto, Y.; Yamagata, S.; Furuse, S. I.; Hayase, H.; Echigo, T.; Iwata, C. J. Chem. Soc., Chem. Commun. 1998, 651.
24. (e) Durand, A.-C.; Rodriguez, J.; Dulcere, J.-P. Synlett 2000, 731 and references therein.
25. Nair, V.; Balagopal, L.; Sheeba, V.; Panicker, S. B.; Rath, N. P. Chem. Commun. 2001, 1682.
26. Nair, V.; Nair, L. G.; Mathew, J. Tetrahedron Lett. 1998, 39, 2801.
27. Nair, V.; Mathew, J.; Nair, L. G. Synth. Commun. 1997, 27, 3064.
28. (a) Kim, T.; Mirafzal, G. A.; Liu, J.; Bauld, N. L. J. Am. Chem. Soc. 1993, 115, 7653.
29. (b) Schepp, N. P.; Shukla, D.; Sarker, H.; Bauld, N. L.; Johnston, L. J. J. Am. Chem. Soc. 1997, 119, 10325.