Title of article :
Efficient, enantioselective synthesis of a β,β-disubstituted carboxylic acid by Ru-XylPhanePhos-catalyzed asymmetric hydrogenation
Author/Authors :
Grasa، نويسنده , , Gabriela A. and Zanotti-Gerosa، نويسنده , , Antonio and Ghosh، نويسنده , , Shyamali and Teleha، نويسنده , , Christopher A. and Kinney، نويسنده , , William A. and Maryanoff، نويسنده , , Bruce E.، نويسنده ,
Abstract :
Enantioselective preparation of a key αvβ3 integrin antagonist intermediate was accomplished via catalytic asymmetric hydrogenation of the corresponding β,β-disubstituted α,β-unsaturated carboxylic acid bearing a 3-quinolinyl moiety. The successful application of a Ru-(R)-XylPhanePhos catalyst to this type of substrate is unprecedented. In situ NMR experiments of pre-catalyst formation/activation by CH3CO2H, and reaction parameter modification, revealed that [Ru(COD)(CF3CO2)2]2/(R)-XylPhanePhos is a highly active and efficient catalytic system.
