Gamma-p-toluenesulfonyl-alpha,beta-epoxysilane: a new and practical acrolein beta-anion equivalent.
[reaction: see text] Reaction of gamma-p-toluenesulfonyl-alpha,beta-epoxysilane with alkyl halides and aldehydes followed by treatment with n-Bu4NF affords alpha,beta-unsaturated aldehydes via a Brook rearrangement-mediated tandem process under extremely mild conditions.
Sasaki
Michiko
M
Department of Synthetic Organic Chemistry, Graduate School of Medical Sciences, Hiroshima University, 1-2-3 Kasumi, Minami-Ku, Hiroshima 734-8551, Japan.
Takeda
Kei
K
D000171:Acrolein / Q000031:analogs & derivatives / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry; D006846:Hydrocarbons, Halogenated / Q000737:chemistry; D015394:Molecular Structure; D012821:Silanes / Q000138:chemical synthesis / Q000737:chemistry*; D014105:Tosyl Compounds / Q000138:chemical synthesis / Q000737:chemistry*
D000447:Aldehydes; D006846:Hydrocarbons, Halogenated; D012821:Silanes; D014105:Tosyl Compounds; C510304:gamma-p-toluenesulfonyl-alpha,beta-epoxysilane; D000171:Acrolein