New evidence on the regiochemistry of the tert-butyldiphenylsilylcupration of allene using the silylcuprate or silylcopper reagent

Tetrahedron

Volumn 59, Issue 31, 2003, Pages 5855-5859

  Cuadrado, Purificación ^a   González Nogal, Ana M ^a   Sánchez, Alicia ^a   Sarmentero, M Angeles ^a  

^a UNIVERSITY OF VALLADOLID   (Spain)

Author keywords

Allene; Allylsilanes; Silylcupration; Vinylsilanes

Indexed keywords

1 [2 (TERT BUTYLDIPHENYLSILYL)PROP 2 EN 1 YL]CYCLOHEX 2 ENOL; 3 (TERT BUTYLDIPHENYLSILYL) 2 METHYLPROPENE; 3 [(TERT BUTYLDIPHENYLSILYL)METHYL]BUT 3 EN 2 ONE; 3 [3 (TERT BUTYLDIPHENYLSILYL)PROP 1 EN 2 YL]CYCLOHEXENONE; 4 (TERT BUTYLDIPHENYLSILYL) 2 METHYLPENT 4 EN 2 OL; 4 (TERT BUTYLDIPHENYLSILYL)PENT 4 EN 2 OL; 4 [(TERT BUTYLDIPHENYLSILYL)METHYL] 1 PHENYLPENTA 1,4 DIEN 3 OL; 4 [(TERT BUTYLDIPHENYLSILYL)METHYL] 3 PHENYLPENT 4 ENAL; 5 (TERT BUTYLDIPHENYLSILYL) 1 PHENYLHEXA 1,5 DIEN 3 OL; 5 (TERT BUTYLDIPHENYLSILYL) 3 METHYLHEXA 1,5 DIEN 3 OL; 5 [(TERT BUTYLDIPHENYLSILYL)METHYL] 4 PHENYLHEX 5 EN 2 ONE; ALLENE DERIVATIVE; COPPER DERIVATIVE; REAGENT; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CONJUGATION; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; TEMPERATURE;

EID: 0038446042     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)00945-1     Document Type: Article

References (11)

1. Barbero A., Cuadrado P., González A.M., Pulido F.J., Fleming I. J. Chem. Soc. Perkin Trans. I. 1991;2811-2816.
2. Barbero A., Cuadrado P., Fleming I., González A.M., Pulido F.J., Sánchez A. J. Chem. Soc. Perkin Trans. I. 1995;1525-1532.
3. Blanco F.J., Cuadrado P., González A.M., Pulido F.J., Fleming I. Tetrahedron Lett. 35:1994;8881-8882.
4. For leading references to the reactivity of allyl and vinylsilanes, see: (a) Chan T.H., Fleming I. Synthesis. 1979;761. (b) Weber W.P. Silicon Reagents for Organic Synthesis. Springer, Berlin, 1983; pp 79-108 and 173-201.
5. For leading references to the reactivity of allyl and vinylsilanes, see: (a) Chan T.H., Fleming I. Synthesis. 1979;761. (b) Weber W.P. Silicon Reagents for Organic Synthesis. Springer, Berlin, 1983; pp 79-108 and 173-201.
6. In the course of our investigations concerning the behavior toward electrophiles of dimetalated alkenes bearing silicon groups in a vinylic and allylic position, we have substituted the allylic tert-butyldiphenylsilyl group in the presence of a vinylic tert-butyl diphenylsilyl or even a better electrofugal group like dimethylphenylsilyl. These results will be published as soon as possible.
7. (a) Trost B.M., Coppola B.P. J. Am. Chem. Soc. 104:1982;6879
8. (b) Schinzer D. Synthesis. 1988;263.
9. (a) Denmark S.E., Jones T.K. J. Am. Chem. Soc. 104:1982;2642
10. (b) Denmark S.E., Wallace M.A., Walker C.B. J. Org. Chem. 55:1990;5543. and references cited therein.
11. Fleming I., Dunoguès J., Smithers R. Org. React. 37:1989;57-575.