PET-Oxidative cyclization of unsaturated silyl enol ethers. Regioselective control by solvent effects

Tetrahedron Letters

Volumn 37, Issue 41, 1996, Pages 7349-7352

  Hintz, Sandra ^a   Fröhlich, Roland ^b   Mattay, Jochen ^a  

^a UNIVERSITY OF KIEL   (Germany)

^b UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

INDAN DERIVATIVE; POLYCYCLIC HYDROCARBON;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; PHOTOCHEMISTRY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 16044362070     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01708-X     Document Type: Article

References (17)

1. 1. Hintz, S.; Heidbreder, A.; Mattay, J. "Radical Ion Cyclizations"; Top. Curr. Chem. 1996, 177, 77.
2. 2. Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 734.
3. 3. Beckwith, L. A. J. Tetrahedron 1981, 37, 3073.
4. 4. Guo, Q. X.; Qin, X. Z.; Wang, J. T.; Williams, F. J. Am. Chem. Soc. 1988, 110, 1974.
5. 5. Hudson, C. M.; Marzabadi, M. R.; Moeller, K. D.; New, D. G. J. Am. Chem. Soc. 1991, 113, 7372.
6. 6. Hudson, C. M.; Moeller, K. D. J. Am. Chem. Soc. 1994, 116, 3347.
7. 7. Shono, T.; Nishiguchi, I.; Kashimura, S.; Okawa, M. Bull. Chem. Soc. Jpn. 1978, 51, 2181.
8. OX [1] = +1.58 V vs. Ag/AgCl.
9. 9. Snider, B. B.; Kwon, T. J. Org. Chem. 1990, 55, 4786.
10. 10. Snider, B. B.; Kwon, T. J. Org. Chem. 1992, 57, 2399.
11. 11. Heidbreder, A.; Mattay, J. Tetrahedron Lett. 1992, 33, 1973.
12. 12. Heidbreder, A.; Mattay, J. J. Inf. Rec. Mats. 1994, 21, 575.
13. 13. Horiguchi, Y.; Matsuzawa, S. Tetrahedron Lett. 1986, 27, 4025.
14. 14. The nucleophile assisted Si-O bond cleavage of sily1 enol ether radical cations have been recently confirmend using cyclic voltametry: Schmittel, M.; Keller, M.; Burghart, A. J. Chem. Soc., Perkin Trans 1, 1995, 2315.
15. 15. Jeon, Y. T.; Lee, C.-P.; Mariano, P. S. J. Am. Chem. Soc. 1991, 113, 8847.
16. 2 = 0.128 for all reflections. Further information can be obtained from the Fachinfomationszentrum Karlsruhe, D-76344 Eggenstein-Leopoldshafen, on quoting the depository number CSD-404816. Characteristic bond lengths and angles:C(4)-O 1.218(3), C(4)-C(4A) 1.512(3), O-C(4)-C(3) 112.3(2), C(5A)-C(4A)-C(10A) 112.4(2).
17. 8-H).