95547-16-3Relevant articles and documents
A novel synthesis of β-ketosilanes via organoboranes
Bhat,Martinez,De Los Santos
, p. 6541 - 6544 (2000)
A convenient, novel synthesis of β-ketosilanes based on (Z)-1-bromo-1-alkenylboronate esters is developed. α-Bromo-(Z)-1-alkenylboronate esters readily available using literature procedures smoothly undergo a reaction with trimethylsilylmethyllithium in tetrahydrofuran to provide the corresponding 'ate' complexes. These 'ate' complexes will undergo intramolecular nucleophilic substitution reactions to afford the corresponding (E)-trisubstituted olefins containing trimethylsilylmethyl moiety. The oxidation of these intermediates with sodium acetate and hydrogen peroxide provides β-ketosilanes in good yields (63-75% yield). (C) 2000 Elsevier Science Ltd.
Reaction of acylsilanes with sulfur ylides. Selective formation of silyl enol ethers or β-ketosilanes
Nakajima, Tadashi,Segi, Masahito,Sugimoto, Fumitosi,Hioki, Reiko,Yokota, Seiko,Miyashita, Kiyoshi
, p. 8343 - 8358 (2007/10/02)
The reaction of acylsilanes with sulfur ylides in THF results in the formation of the corresponding silyl enol ethers or β-ketosilanes. The relative ratio of these products varies with the ylide conditions and the stability of ylide used. It is noteworthy that silyl enol ethers were formed under the salt-free ylide conditions, and that β-ketosilanes were yielded in the presence of soluble inorganic salts in THF, selectively. The formation of both products would be interpreted in terms of the anionotropic and cationotropic rearrangements of silyl group in the reaction intermediate.
Selective formation of alkenes from trimethylsilylmethyl ketones and from acylsilanes
Fuerstner, Alois,Kollegger, Gerlinde,Weidmann, Hans
, p. 295 - 305 (2007/10/02)
Trimethylsilylmethyl ketones, readily available from acyl chlorides, undergo a Reformatsky-Peterson reaction sequence to give 3-alkenoates regioselectively.Acylsilanes, however, react with either zinc ester enolates or trimethylsilylmethylmagnesium chloride to give the corresponding tertiary alcohols which, depending on their structure, spontaneously undergo either elimination or a Brook rearrangement-Peterson olefination sequence.These reactions allow the selective formation of vinylsilanes.