Trimethylsilylcyanation of Aldehydes and Ketones Catalyzed by Alkali Metal Fluorides and N-Methylmorphorine-N-Oxide

초록

Chiral cyanohydrins are useful intermediates because the two functional groups could be easily transformed into various homochiral ones. This includes ?hydroxy acids1,2, ?hydroxy aldehydes?, ?hydroxy ketones3, ?hydroxy amines2,3 and ?amino acid derivatives4. A number of catalysts for the asymmetric addition of cyanide to aldehydes5 have been known to include synthetic peptides and chiral transition metal complexes. Numerous aldehydes and ketones undergo achiral silylcyanation with (CH3)3SiCN that is catalyzed by KF6, CsF7,8, and N-methylmorpholine-N-Oxide9,10, respectively