Cationic [5+2] cycloaddition reactions promoted by trimethylsilyl triflate in highly polar media

Tetrahedron Letters

Volumn 38, Issue 8, 1997, Pages 1321-1324

  Collins, Jon L ^a   Grieco, Paul A ^a   Walker, John K ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO[3.2.1]OCTANE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; REACTION ANALYSIS;

EID: 0031584914     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00030-0     Document Type: Article

References (12)

1. 1. Walls, F.; Padilla, J.; Joseph-Nathan, P.; Giral, F.; Romo, J. Tetrahedron Lett. 1965, 1577.
2. 2. Büchi, G.; Mak, C.-P. J. Am. Chem. Soc. 1977, 99, 8073.
3. 3. Büchi, G.; Chu, P.-S. Tetrahedron 1981, 37, 4509.
4. 4. Engler, T.A.; Combrink, K.D.; Takusagawa, F. J. Chem. Soc., Chem. Commun. 1989, 1573. Engler, T.A.; Combrink, K.D.; Letavic, M.A.; Lynch, K.O., Jr.; Ray, J.E. J. Org. Chem. 1994, 59, 6567.
5. 4. Engler, T.A.; Combrink, K.D.; Takusagawa, F. J. Chem. Soc., Chem. Commun. 1989, 1573. Engler, T.A.; Combrink, K.D.; Letavic, M.A.; Lynch, K.O., Jr.; Ray, J.E. J. Org. Chem. 1994, 59, 6567.
6. 5. Grieco, P.A.; Nunes, J.J.; Gaul, M.D. J. Am. Chem. Soc. 1990, 112, 4595. Grieco, P.A.; Handy, S.T.; Beck, J.P. Tetrahedron Lett. 1994, 35, 2663. Grieco, P.A., Aldrichim. Acta 1991, 24, 59. Also see: Grieco, P. A. Organic Chemistry in Lithium Perchlorate/Diethyl Ether. In Organic Chemistry: Its Language and Its State of the Art; Kisakürek, V., Ed.;VCH: Basel, 1993; p. 133.
7. 5. Grieco, P.A.; Nunes, J.J.; Gaul, M.D. J. Am. Chem. Soc. 1990, 112, 4595. Grieco, P.A.; Handy, S.T.; Beck, J.P. Tetrahedron Lett. 1994, 35, 2663. Grieco, P.A., Aldrichim. Acta 1991, 24, 59. Also see: Grieco, P. A. Organic Chemistry in Lithium Perchlorate/Diethyl Ether. In Organic Chemistry: Its Language and Its State of the Art; Kisakürek, V., Ed.;VCH: Basel, 1993; p. 133.
8. 5. Grieco, P.A.; Nunes, J.J.; Gaul, M.D. J. Am. Chem. Soc. 1990, 112, 4595. Grieco, P.A.; Handy, S.T.; Beck, J.P. Tetrahedron Lett. 1994, 35, 2663. Grieco, P.A., Aldrichim. Acta 1991, 24, 59. Also see: Grieco, P. A. Organic Chemistry in Lithium Perchlorate/Diethyl Ether. In Organic Chemistry: Its Language and Its State of the Art; Kisakürek, V., Ed.;VCH: Basel, 1993; p. 133.
9. 5. Grieco, P.A.; Nunes, J.J.; Gaul, M.D. J. Am. Chem. Soc. 1990, 112, 4595. Grieco, P.A.; Handy, S.T.; Beck, J.P. Tetrahedron Lett. 1994, 35, 2663. Grieco, P.A., Aldrichim. Acta 1991, 24, 59. Also see: Grieco, P. A. Organic Chemistry in Lithium Perchlorate/Diethyl Ether. In Organic Chemistry: Its Language and Its State of the Art; Kisakürek, V., Ed.;VCH: Basel, 1993; p. 133.
10. 6. Grieco, P.A.; Collins, J.L.; Moher, E.D.; Fleck, T.J.; Gross, R.S. J. Am. Chem. Soc. 1993, 115, 6078.
11. 7. The ethyl acetate is distilled from calcium hydride prior to use.
12. 8. Prepared according to the procedure of Büchi: Büchi, G.; Chu, P.-S.; Hoppmann, A.; Mak, C.-P.; Pearce, A. J. Org. Chem. 1978, 43, 3983.