158637-75-3Relevant academic research and scientific papers
Facile syntheses of α-bromo-α-silyl ketones and α-bromoacylsilanes from tert-butyldimethylsilyldibromomethane and carbonyl compounds
Shinokubo, Hiroshi,Oshima, Koichiro,Utimoto, Kiitiro
, p. 14533 - 14542 (1996)
An addition of benzaldehyde to an ethereal solution of tert-butyldimethylsilyldibromomethyllithium, derived from t-BuMe2SiCHBr2 and lithium diisopropylamide, provided α-bromo-α-silyl ketone. The use of ketone instead of aldehyde afforded α-bromoacylsilane via a bromo silyl epoxide intermediate. Further treatment of the α-bromo-α-silyl ketone with butyllithium afforded lithium enolate which provided β-hydroxy-α-silyl ketone upon treatment with aldehyde in ether. The enolate gave α,β-unsaturated ketone or monosilyl ether of 2-acyl-1,3-diol in THF instead of ether. The use of isopropylmagnesium bromide in place of butyllithium also resulted in a formation of the corresponding magnesium enolate.
One-pot synthesis of α,β-unsaturated ketones from tert- butyldimethylsilyldibromomethane and two different aldehydes
Shinokubo,Oshima,Utimoto
, p. 3741 - 3744 (2007/10/02)
An addition of benzaldehyde to an ethereal solution of tert- butyldimethylsilyldibromomethyllithium provided α-bromo-α-silyl ketone. Further treatment of the α-bromo-α-silyl ketone with butyllithium afforded enolate which provided β-hydroxy-α-silyl ketone upon treatment with aldehyde in ether. The enolate gave α,β-unsaturated ketone or monosilyl ether or 2-acyl-1,3-diol in THF instead of ether.
