1185262-59-2Relevant 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.
Lanthanum tricyanide-catalyzed acyl silane - Ketone benzoin additions
Tarr, James C.,Johnson, Jeffrey S.
supporting information; experimental part, p. 3870 - 3873 (2009/12/06)
Figur Presented Lanthanum tricyanide efficiently catalyzes a benzoin-type coupling between acyl silanes and ketones. Yields range from moderate to excellent over a broad substrate scope encompassing aryl, alkyl, electron-rich, and sterically hindered keto
