Acid-catalyzed intramolecular addition of a carboxy group to vinylsilanes

Journal of Organometallic Chemistry

Volumn 686, Issue 1-2, 2003, Pages 242-250

  Miura, Katsukiyo ^a,b   Hayashida, Joji ^a,b   Takahashi, Tatsuyuki ^a,b   Nishikori, Hisashi ^a,b   Hosomi, Akira ^a,b  

^a UNIVERSITY OF TSUKUBA   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

lactone; Acid Catalyst; Cyclization; Vinylsilane

Indexed keywords

ACID; ALLYL COMPOUND; CARBON; CARBOXYL GROUP; CHLORINE DERIVATIVE; GAMMA LACTONE DERIVATIVE; SILANE DERIVATIVE; TITANIUM DERIVATIVE; VINYL DERIVATIVE;

ADDITION REACTION; ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; CYCLIZATION; GEOMETRY; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SUBSTITUTION REACTION;

EID: 0142120324     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(03)00533-3     Document Type: Article

References (20)

1. Brook M.A. Silicon in Organic, Organometallic Polymer Chemistry 2000 571 Wiley New York
2. Bassindale A.R. Taylor P.G. in: Patai S. Rappoport Z. (Eds.) The Chemistry of Organic Silicon Compounds 1989 893 (Part 2) Wiley Chichester (Part 2)
3. Miura, K. Hosomi, A. Synlett (2003) 143.
4. Miura K. Okajima S. Hondo T. Nakagawa T. Takahashi T. Hosomi A. J. Am. Chem. Soc. 122 2000 11348
5. Miura, K. Takahashi, T. Nishikori, H. Hosomi, A. Chem. Lett. (2001) 958.
6. Miura K. Hondo T. Nakagawa T. Takahashi T. Hosomi A. Org. Lett. 2 2000 385
7. Miura K. Hondo T. Takahashi T. Hosomi A. Tetrahedron Lett. 41 2000 2129
8. Miura K. Hondo T. Okajima S. Nakagawa T. Takahashi T. Hosomi A. J. Org. Chem. 67 2002 6082
9. Miura K. Takahashi T. Hondo T. Hosomi A. Chirality 15 2003 41
10. Ansell M.F. Palmer M.H. Quart. Rev. 18 1964 211
11. Fujita T. Watanabe S. Suga K. Miura T. Sugahara K. Kikuchi H. J. Chem. Tech. Biotechnol. 32 1982 476
12. Jalander L. Broms M. Acta Chem. Scand. B 36 1982 371
13. Bachi M.D. Epstein J.W. Minzly Y.H.- Loewenthal H.J.E. J Org Chem. 34 1969 126
14. Koenig K.E. Weber W.P. J. Am. Chem. Soc. 95 1973 3416 As mentioned by Koenig and Weber, simultaneously withprotonation to the double bond, rotation would occur aboutthe developing carbon-carbon single bond in the direction topermit the silyl group to continuously stabilize the incipient bsilylcarbeniumion B by hyperconjugation of the Si-C bond.
15. Eliel E.L. Rao V.S. Pietrusiewicz K.M. Org. Magn. Reson. 12 1979 461
16. Anteunis M. Danneels D. Org Magn. Reson. 7 1975 345
17. Schmitt A. Reißig H.-U. Chem. Ber. 128 1995 871
18. Hoffmann R.W. Chem. Rev. 89 1989 1841
19. Corey E.J. Schmidt G. Tetrahedron Lett. 20 1979 399
20. Hudrlik P.F. Peterson D. J. Am. Chem. Soc. 97 1975 1464