Mn(III)-based oxidative free-radical 6-endo cyclizations of Z- trisubstituted alkenes

Tetrahedron

Volumn 54, Issue 36, 1998, Pages 10641-10648

  Snider, Barry B ^a   Kiselgof, Jane Y ^a  

^a BRANDEIS UNIVERSITY   (United States)

Author keywords

Cyclization; Radicals and radical reactions

Indexed keywords

ALKENE; CYCLOPENTANE; FREE RADICAL; LACTONE; MANGANESE; PHENANTHRENE;

ARTICLE; CYCLIZATION; ISOMERISM; NUCLEAR MAGNETIC RESONANCE; OXIDATION; PRIORITY JOURNAL; STEREOCHEMISTRY; STEREOSPECIFICITY;

EID: 0032480397     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00612-7     Document Type: Article

References (21)

1. 3 as an oxidant see: (a) Snider, B. B. Chem. Rev. 1996, 96, 339.
2. (b) Melikyan, G. G. In Organic Reactions; Paquette, L. A., Ed.; Wiley: New York, 1997; Vol. 49, Chapter 3.
3. 2. Snider, B. B.; Mohan, R. M.; Kates, S. A. J. Org. Chem. 1985, 50, 3659.
4. 3. Snider, B. B.; Mohan, R. M.; Kates, S. A. Tetrahedron Lett. 1987, 28, 841.
5. 4. Zhang, Q.; Mohan, R. M.; Cook, L.; Kazanis, S.; Peisach, D.; Foxman, B. M.; Snider, B. B. J. Org. Chem. 1993, 58, 7640.
6. 5. Burnell, R. H.; Girard, M. Synth. Commun. 1990, 20, 2469.
7. 6. Burnell, R. H.; Côte, C.; Girard, M. J. Nat. Prod. 1993, 56, 461.
8. 7. Shishido, K.; Goto, K.; Tsuda, A.; Takaishi, Y.; Shibuya, M. J. Chem. Soc., Chem. Commun. 1993, 793.
9. 8. Dombroski, M. A.; Kates, S. A.; Snider, B. B. J. Am. Chem. Soc. 1990, 112, 2759.
10. 9. Zoretic, P. A.; Zhang, Y.; Fang, H.; Ribeiro, A. A.; Dubay, G. J. Org. Chem. 1998, 63, 1162 and references cited therein.
11. 10. Julia, M.; Descoins, C.; Baillarge, M.; Jacquet, B.; Uguen, D.; Groeger, F. A. Tetrahedron 1975, 31, 1737.
12. 11. van der Gen, A.; Wiedhaup, K.; Swoboda, J. J.; Dunathan, H. C.; Johnson, W. S. J. Am. Chem. Soc. 1973, 95, 2656.
13. 12. Still, W. C.; Gennari, C. Tetrahedron Lett. 1983, 24, 4405.
14. 13. Fischli, A.; Müller, P. M. Helv. Chim Acta 1980, 63, 529.
15. 14. Cahiez, C.; Alexakis, A.; Normant, J. F. Synthesis 1978, 528.
16. 15. Crabtree, S. R.; Chu, W. L. A.; Mander, L. N. Synlett 1990, 169.
17. 16. Selwood, D. L.; Challand, S. R.; Champness, J. N.; Gillam, J.; Hibberd D. K.; Jandu, K. S.; Lowe, D.; Pether, M.; Selway, J.; Trantor, G. E. J. Med. Chem. 1993, 36, 3503.
18. -1: Jenkins, C. L.; Kochi, J. K. J. Am. Chem. Soc. 1972, 94, 843.
19. 2: Kochi, J. K.; Gilliom, R. D. J. Am. Chem. Soc. 1964, 86, 5251.
20. 18. Curran, D. P.; Morgan, T. M.; Schwartz, C. E.; Snider, B. B.; Dombroski, M. A. J. Am. Chem. Soc. 1991, 113, 6607.
21. 19. Heiba, E. I.; Dessau, R. M.; Koehl, Jr., W. J. J. Am. Chem. Soc. 1969, 91, 138.