Unusually High Reactivity of the C-Si Bond in the Lewis Acid Mediated Reactions of (E)-1-(Trimethylsilyl)-2-(isopropylthio)ethylene with Carbonyl Electrophiles

Synlett

Volumn 1997, Issue 6, 1997, Pages 681-682

  Bonini, Bianca F ^a   Comes Franchini, Mauro ^a   Fochi, Mariafrancesca ^a   Mazzanti, Germana ^a   Ricci, Alfredo ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

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[No Author keywords available]

Indexed keywords

EID: 0003557970     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-3240     Document Type: Article

References (15)

1. Fleming, I.; Dunogués, J.; Smithers, R. Org. React. 1989, 37, 57. Hudrlik, P.F.; Hudrlik, A.M.; Kulkarni, A.K. J. Am. Chem. Soc. 1985, 107, 4260. Colvin, E. in "Silicon in Organic Synthesis", Butterworth, (London), 1981, pp.83-97.
2. Fleming, I.; Dunogués, J.; Smithers, R. Org. React. 1989, 37, 57. Hudrlik, P.F.; Hudrlik, A.M.; Kulkarni, A.K. J. Am. Chem. Soc. 1985, 107, 4260. Colvin, E. in "Silicon in Organic Synthesis", Butterworth, (London), 1981, pp.83-97.
3. Fleming, I.; Dunogués, J.; Smithers, R. Org. React. 1989, 37, 57. Hudrlik, P.F.; Hudrlik, A.M.; Kulkarni, A.K. J. Am. Chem. Soc. 1985, 107, 4260. Colvin, E. in "Silicon in Organic Synthesis", Butterworth, (London), 1981, pp.83-97.
4. Chan, T.H.; Fleming, I. Synthesis 1979, 761. Magnus, P. Aldrichimica Acta 1980, 13, 41.
5. Chan, T.H.; Fleming, I. Synthesis 1979, 761. Magnus, P. Aldrichimica Acta 1980, 13, 41.
6. Ager, D. Tetrahedron Lett. 1982, 23, 1945. Hickmott, P.W. Tetrahedron 1982, 38, 1975.
7. Ager, D. Tetrahedron Lett. 1982, 23, 1945. Hickmott, P.W. Tetrahedron 1982, 38, 1975.
8. Magnus, P.; Quagliato, D. J. Org. Chem. 1985, 50, 1621.
9. Capella, L.; Capperucci, A.; Curotto, G.; Lazzari, D.; Dembech, P.; Reginato, G.; Ricci, A. Tetrahedron Lett. 1993, 34, 3311.
10. Prepared according to: Voronkov, M.G.; Mirskov, R.G.; Rakhil, V.J. Izw. Akad. Nauk. SSSR 1975, 610.
11. 6, gave δ values of -7.08 and -8.02 for 2 and 3 respectively. These results mainly reflect the ground state electronic distribution and are apparently in contrast with the reactivity. This latter depends in fact on the charge distribution in the transition state and in the case of 2 would be greatly affected by the high polarizability of the S atom.
12. These side reactions encountered with vinylsilanes and even more frequently in the Hosomi-Sakurai reactions with allylsilanes are still not fully understood.
13. +), 141, 109, 85.
14. The formation of cyclobutyl derivatives by conjugate addition of allylsilanes to α,β-unsaturated enones has been previously reported: Pardo, R.; Zahra. J.-P., Santelli, M. Tetrahedron Lett. 1979, 47, 4557.
15. Noyori, R.; Murata, S.; Suzuki, M. Tetrahedron 1981, 37, 3899.