72927-87-8Relevant academic research and scientific papers
Clean borrowing hydrogen methodology using hydrotalcite supported copper catalyst
Dixit, Manish,Mishra, Manish,Joshi, Pradyuman A.,Shah, Dinesh O.
, p. 80 - 83 (2013/05/09)
The catalytic activity of Mg-Al hydrotalcite supported copper catalyst was investigated for clean CC and CN bond forming reactions using alcohols as alkylating agent via borrowing hydrogen methodology. The catalyst showed excellent conversion of ketone and amine substrates (71-99%) to alkylated products with high selectivity in alkylation reactions.
Reactions of tin(IV) enolates obtained from O-stannyl ketyls under neutral free radical conditions
Enholm, Eric J.,Whitley, Paul E.,Xie, Yongping
, p. 5384 - 5390 (2007/10/03)
Under mild and neutral free radical conditions, an α,β-unsaturated ketone reacted with tributyltin hydride to produce an intermediate resonance-stabilized allylic O-stannyl ketyl. Upon subsequent hydrogen atom abstraction, a tin(IV) enolate was afforded which could be quenched with a variety of electrophiles and form new carbon-carbon bonds. Aldehydes react to produce aldol-type products and both intramolecular and intermolecular carbonyl addition reactions were investigated using this strategy. Using similar methodology, the tin(IV) enolate could be quenched in the presence of HMPA with various alkyl halides and α,β-unsaturated carbonyl compounds (Michael acceptors) to yield alkylated products in good yields. These reactions represent a very mild regioselective alternative to metal enolate formation which usually requires strong bases such as LDA or strongly reductive dissolving metal conditions to achieve success. New carbon skeletons for natural product synthesis can be readily constructed using this chemically neutral approach.
INTERMOLECULAR ALDOL REACTIONS VIA ALLYLIC O-STANNYL KETYLS
Enholm, Eric J.,Whitley, Paul E.
, p. 9157 - 9160 (2007/10/02)
A mild and neutral free radical reaction of an α,β-unsaturated ketone and tributyltin radical produced a resonance-stabilized allylic O-stannyl ketyl intermediate.A tin(IV)enolate, produced by subsequent hydrogen atom transver, was next quenched with various aldehydes to yield an aldol product which was readily eliminated with p-toluenesulfonic acid to afford new α,β-unsaturated ketones with E/Z ratios up to > 100:1.
