BETA-CYANOSILYLENOLETHERS - PREPARATION AND POTENTIAL INTERMEDIATES IN SYNTHESIS

In a previous paper we reported the direct a-phenylsulfe-nylation of enolates generated during different 1,4-addition reactions on α,β-unsaturated ketones1. Since Nagata has shown that the conjugate addition of a cyano group with diethylaluminum cyanide leads to an aluminum enola-2 te2,3, it would be worthwile to investigate the potentiality of this reagent for simultaneous functionalisation at the a-position. Initial experiments for in situ trapping with phenylsulfenylchloride gave disappointing low yields (< 15 %). However working up the initially formed aluminumenolate with trimethylchlorosilane and pyridine afforded the corresponding silylenolethers in 4 very good yields (Table I). © 1978, Taylor & Francis Group, LLC. All rights reserved.