Silicon in synthesis—17: Chloromethyl (trimethylsilyl) lithium—anew reagent for the direct conversion of aldehydes and ketones into⇌, β,-epoxytrimethylsilanes
C Burford, F Cooke, G Roy, P Magnus
Index: Burford, Clifford; Cooke, Frank; Roy, Glenn; Magnus, Philip Tetrahedron, 1983 , vol. 39, # 6 p. 867 - 876
Full Text: HTML
Citation Number: 57
Abstract
Treatment of chloromethyltrimethylsilane 1 with sec-BuLi in THF at-78° produces chloromethyl (tri-methylsilyl) lithium 4. Treatment of 4 with a wide range of aldehydes and ketones gives⇌, β-epoxytrimethylsilanes 5–28, which on acidic hydrolysis give homologated aldehydes.
Related Articles:
Rhodium complex catalyzed hydroformylation reactions of linear and cyclic mono-and diolefins
[Trzeciak, Anna M.; Ziolkowski, Jozef J. Journal of Organometallic Chemistry, 1994 , vol. 479, # 1-2 p. 213 - 216]
18-Cycloalkyl analogs of enisoprost
[Collins, Paul W.; Gasiecki, Alan F.; Perkins, Willam E.; Gullikson, Gary W.; Jones, Peter H.; Bauer, Raymond F. Journal of Medicinal Chemistry, 1989 , vol. 32, # 5 p. 1001 - 1006]
[Vincek, William C.; Aldrich, Constance S.; Borchardt, Ronald T.; Grunewald, Gary L. Journal of Medicinal Chemistry, 1981 , vol. 24, # 1 p. 7 - 12]
[Buechi,G.; Burgess,E.M. Journal of the American Chemical Society, 1962 , vol. 84, p. 3104 - 3109]
[Buechi,G.; Burgess,E.M. Journal of the American Chemical Society, 1962 , vol. 84, p. 3104 - 3109]