76837-19-9Relevant academic research and scientific papers
Trimethylsilyl Cyanide - A Reagent for Umpolung, V. Nucleophilic Acylation of Alkylating Reagents with α,β-Unsaturated Aldehydes.
Hertenstein, Ulrich,Huenig, Siegfried,Oeller, Manfred
, p. 3783 - 3802 (2007/10/02)
The readily accessible adducts 3 from α,β-unsaturated aldehydes and trimethylsilyl cyanide react smoothly after deprotonation (LDA) as anions 3A with different alkylating agents in 1-position.Removal of the protective group under mild conditions yields the α,β-unsaturated ketones 5 in 60 - 80 percent overall yield.The stability of anions 3A is increased by an O-triethylsilyl group.Alkylation of 3A in 3-position (partly) is caused by 3-acceptor substituents.Nucleophilic acylation with α-alkoxyaldehydes produces 1,2-diketones via a new route.
