The allylation of acylsilanes with tetraallyltin in the presence of catalytic amounts of Sc(OTf)3 proceeded smoothly to afford the silylated homoallylic alcohols in good yields. Subsequent protiodesilylation gave the formal adducts of the corresponding aldehydes. The homochiral acylsilane 11 gave a reversal of asymmetric induction in the Sc(OTf)3 catalyzed allylation and in the Sakurai reaction.
Bonini B.F., Comes-Franchini M., Fochi M., Mazzanti G., Nanni C., Ricci A. (1998). Allylation reactions of acylsilanes as synthetic equivalents of aldehydes. Application of a stereocontrolled synthesis of (1S,2S,5S)-(10S)- and-(10R)-allyl myrtanol. TETRAHEDRON LETTERS, 39(37), 6737-6740 [10.1016/S0040-4039(98)01413-0].
Allylation reactions of acylsilanes as synthetic equivalents of aldehydes. Application of a stereocontrolled synthesis of (1S,2S,5S)-(10S)- and-(10R)-allyl myrtanol
Bonini B. F.;Comes-Franchini M.;Fochi M.;Mazzanti G.;Ricci A.
1998
Abstract
The allylation of acylsilanes with tetraallyltin in the presence of catalytic amounts of Sc(OTf)3 proceeded smoothly to afford the silylated homoallylic alcohols in good yields. Subsequent protiodesilylation gave the formal adducts of the corresponding aldehydes. The homochiral acylsilane 11 gave a reversal of asymmetric induction in the Sc(OTf)3 catalyzed allylation and in the Sakurai reaction.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
