Enantioselective [3+2] Cycloaddition of Donor‐Acceptor Aziridines and Imines to Construct 2,5‐<i>trans</i>‐Imidazolidines
Jianglin Qiao, Shiyu Wang, Xiaohua Liu, Xiaoming Feng
Abstract
Abstract An enantioselective [3+2] cycloaddition of donor‐acceptor aziridines with N ‐aryl protected imines was developed with a Ni(ClO 4 ) 2 ⋅ 6H 2 O/ N , N′ ‐dioxide catalyst system, providing a broad range of chiral trans ‐substituted imidazolidine compounds with good yields and excellent enantioselectivities (up to 99 % yield, up to 98 % ee). Control experiments indicated that the products could offer excellent diastereoselectivities with the control of chiral Ni(II)‐ N , N′ ‐dioxide complex and the interaction of the substrates. The possible catalytic process was proposed to rationalize the stereocontrol.
Topics & Concepts
Enantioselective synthesisCycloadditionImidazolidineCatalysisChemistryYield (engineering)AcceptorArylCombinatorial chemistryMedicinal chemistryOrganic chemistryMaterials scienceAlkylPhysicsMetallurgyCondensed matter physicsSynthesis and Catalytic ReactionsCatalytic C–H Functionalization MethodsAsymmetric Synthesis and Catalysis