Enantioselective Synthesis of Azetidines through [3 + 1]-Cycloaddition of Donor–Acceptor Aziridines with Isocyanides
Fengcai Zhang, Xinpeng Sang, Yuqiao Zhou, Weidi Cao, Xiaoming Feng
Abstract
The enantioselective [3 + 1]-cycloaddition of racemic donor–acceptor (D–A) aziridines with isocyanides was first realized under mild reaction conditions using a chiral N,N′-dioxide/MgII complex as catalyst, providing a facile route to enantioenriched exo-imido azetidines with good to excellent yield (up to 99%) and enantioselectivity (up to 94% ee). An obvious chiral amplification effect was observed in this system, and an explanation was elucidated based on the experimental investigation and X-ray crystal structure of the enantiomerically pure catalyst.
Topics & Concepts
Enantioselective synthesisCycloadditionChemistryCatalysisYield (engineering)AcceptorCombinatorial chemistryStereoisomerismStereochemistryOrganic chemistryMaterials sciencePhysicsMetallurgyCondensed matter physicsSynthesis and Catalytic ReactionsAsymmetric Synthesis and CatalysisCatalytic C–H Functionalization Methods