Molybdenum-Catalyzed Regio- and Enantioselective Amination of Allylic Carbonates: Total Synthesis of (<i>S</i>)-Clopidogrel
Shahid Khan, Junjie Zhang, Ajmal Khan
Abstract
The first molybdenum-catalyzed highly regio- and enantioselective allylic amination of both aryl- and alkyl-substituted branched allylic carbonates has been developed. A wide variety of amines, including drugs and complex bioactive molecules, underwent successful amination with excellent reaction outcomes (up to 96% yield, >99% ee, and >20:1 b/l). The reaction could be scaled up and has been applied to the total synthesis of chiral drug molecule ( S )-clopidogrel (Plavix).
Topics & Concepts
AminationEnantioselective synthesisAllylic rearrangementChemistryCatalysisYield (engineering)ArylMolybdenumTotal synthesisOrganic chemistryCombinatorial chemistryMedicinal chemistryAlkylMetallurgyMaterials scienceAsymmetric Hydrogenation and CatalysisSynthesis and Catalytic ReactionsAsymmetric Synthesis and Catalysis