Catalytic asymmetric synthesis of enantioenriched α-deuterated pyrrolidine derivatives
Xin Chang, Xiang Cheng, Chun‐Jiang Wang
Abstract
-metallated α-deuterated azomethine ylide species for the ensuing 1,3-DC are crucial to the success of α-deuterated chiral pyrrolidine synthesis. The current protocol exhibits remarkable features, such as readily available substrates, inexpensive and safe deuterium source, mild reaction conditions, and easy manipulation. Notably, the synthetic utility of a reversed 1,3-DC/[H/D-Ex] protocol has been demonstrated by catalytic asymmetric synthesis of deuterium-labelled MDM2 antagonist idasanutlin (RG7388) with high deuterium incorporation.
Topics & Concepts
ChemistryPyrrolidineDeuteriumStereocenterCatalysisCombinatorial chemistryEnantioselective synthesisAzomethine ylideStereochemistryCycloadditionOrganic chemistry1,3-Dipolar cycloadditionPhysicsQuantum mechanicsChemical Reactions and IsotopesAsymmetric Hydrogenation and CatalysisChemical Synthesis and Analysis