Reactivity of dichlorosilanes with lithium ester enolates: synthesis of 3,3-disubstituted 3-silaglutarates

Article abstract of DOI:10.1016/0022-328X(94)24757-A

3,3-Disubstituted 3-silaglutarates were synthesized by reaction of the lithium enolate of ethyl acetate with dichlorosilanes at -94 deg C.When a phenyl group is linked to the silicon atom the reaction in THF gave mainly the silaglutarate.In other cases alkylsilylketene acetals were formed in proportions similar to or greater than that of the silaglutarate.The presence of HMPA increased the ratio of C- to O-silylated products and allowed the preparation of 3,3-dialkyl 3-silaglutarates in good yield.Keywords: 3-silaglutarates; Dichlorosilanes; Lithium enolates