121788-91-8Relevant articles and documents
Ttimethylsilyl Cyanide - A Reagent for Umpolung, XVIII. - Nucleophilic Acylation of α-Chlorocarbonyl Compounds - a Novel and Diastereoselective Approach to Substituted α,β-Epoxy Ketones
Huenig, Siegfried,Marschner, Claus
, p. 107 - 114 (2007/10/02)
The addition products of trimethylsilyl cyanide and benzaldehyde (1a), furfural (1b), and α,β-unsaturated aldehydes 2a-c, respectively, react after deprotonation with α-chloroaldehydes and -ketones 3a-d.By 1,4-O,O-silyl rearrangement and cyanide elimination O-trimethylsilyl acyloins 4 and 9, respectively, are formed.With fluoride, 4 and 9 react to α,β-epoxy ketones 5 and 10 in high yield and with E/Z selectivities from 80:20 to >95:5.By this novel route even α,β-unsaturated epoxy ketones (10) become available.