59386-47-9Relevant academic research and scientific papers
Alkylation of magnesium enamide with alkyl chlorides and fluorides
Hatakeyama, Takuji,Ito, Shingo,Nakamura, Masaharu,Nakamura, Eiichi
, p. 14192 - 14193 (2005)
A magnesium enamide derived from N-2-(N′,N′-diethylamino)ethyl imine reacts with a primary and secondary alkyl chloride or a primary alkyl fluoride to give an α-alkylated ketone in good to excellent yield after hydrolysis. The reaction takes place with a high level of inversion of stereochemistry at the electrophilic carbon center and will be useful for production of optically active compounds. Copyright
Regioselective α-alkylation of ketones with alkyl chlorides and fluorides via highly nucleophilic magnesium enamides
Hatakeyama, Takuji,Ito, Shingo,Yamane, Hiroaki,Nakamura, Masaharu,Nakamura, Eiichi
, p. 8440 - 8448 (2008/02/08)
A magnesium enamide derived from N-2-(N′,N′-dimethylamino)ethyl imine reacts with primary and secondary alkyl chlorides and fluorides to give an α-alkylated ketone in good to excellent yields upon hydrolysis of the imine moiety. Reactions of the highly nucleophilic magnesium enamide derived from an unsymmetrical ketone take place regioselectively. In addition, the C-C bond formation is stereospecific: a substantial inversion of stereochemistry at the electrophilic carbon center (Walden inversion) was observed, proving its potential utility for the production of optically active compounds.
Enzymatic resolution of bicyclo[n.1.0]alkan-1-ols derivatives: Preparation of optically active α-substituted α-methylcycloalkanones
Morisson,Barnier,Blanco
, p. 7749 - 7764 (2007/10/03)
Optically active α-methyl α-substituted cycloalkanones are prepared by a chemoenzymatic sequence which involves a Lipozyme-catalyzed transesterification of 1-(chloroacetoxy)bicyclo[n.1.0]alkanes and ring opening of these cyclopropanol derivatives.
