4338-69-6Relevant academic research and scientific papers
Lanthanum tricyanide-catalyzed acyl silane-ketone benzoin additions and kinetic resolution of resultant α-silyloxyketones
Tarr, James C.,Johnson, Jeffrey S.
supporting information; experimental part, p. 3317 - 3325 (2010/08/05)
We report the full account of our efforts on the lanthanum tricyanide-catalyzed acyl silane-ketone benzoin reaction. The reaction exhibits a wide scope in both acyl silane (aryl, alkyl) and ketone (aryl-alkyl, alkyl-alkyl, aryl-aryl, alkenyl-alkyl, alkynyl-alkyl) coupling partners. The diastereoselectivity of the reaction has been examined in both cyclic and acyclic systems. Cyclohexanones give products arising from equatorial attack by the acyl silane. The diastereoselectivity of acyl silane addition to acyclic α-hydroxy ketones can be controlled by varying the protecting group to obtain either Felkin-Ahn or chelation control. The resultant α-silyloxyketone products can be resolved with selectivity factors from 10 to 15 by subjecting racemic ketone benzoin products to CBS reduction.
Rhodium-catalyzed addition of arylstannanes to carbon-heteroatom double bond
Oi, Shuichi,Moro, Mitsutoshi,Fukuhara, Hiroe,Kawanishi, Takanori,Inoue, Yoshio
, p. 4351 - 4361 (2007/10/03)
The addition of arylstannanes to the carbon-heteroatom double bond in the presence of a catalytic amount of a cationic rhodium complex ([Rh(cod)(MeCN)2]BF4) was examined. The reactions of aldehydes, α-dicarbonyl compounds, and N-substituted aldimines with the arylstannanes gave corresponding alcohols, α-hydroxy carbonyl compounds, and amines, respectively. An arylrhodium complex generated by the transmetalation with the arylstannane was probably the active catalytic species.
Samarium(II) iodide-promoted intermolecular and intramolecular ketone- nitrile reductive coupling reactions
Zhou, Longhu,Zhang, Yongmin,Shi, Daqing
, p. 91 - 98 (2007/10/03)
Samarium (II) iodide, a strong one-electron transfer reducing reagent, has been successfully utilized for the intermolecular and intramolecular reductive coupling reactions of ketones with nitriles, α-Hydroxy ketones, monocyclic, fused bicyclic α-hydroxy ketones and monocyclic α-amino alcohols composed of a number of substitution patterns have been prepared in good yields at room temperature or reflux under neutral conditions. The procedure can avoid overreduction of the resulting of α-hydroxy ketones or α-amino alcohols. The crystal structures of monocyclic α-amino alcohols are reported.
