Organic Chemistry Portal



P(NMe2)3-Mediated Aziridination of Imines with α-Ketoesters for Synthesis of Aziridine-2-carboxylates

Jin Jiang, Hui Liu, Chong-Dao Lu* and Yan-Jun Xu*

*Key Laboratory of Plant Resources and Chemistry of Arid Zones, Xinjiang Technical Institute of Physics & Chemistry, Chinese Academy of Sciences, Urumqi 830011, China, Email:,

J. Jiang, H. Liu, C.-D. Lu, Y.-J. Xu, J. Org. Chem., 2017, 82, 811-818.

DOI: 10.1021/acs.joc.6b02669

see abstract for more reactions


Adducts derived from P(NMe2)3 and α-ketoesters are effectively intercepted by N-sulfonyl imines, affording a range of aziridine-2-carboxylates. The diastereoselectivity of this aziridination depends on steric hindrance from substituents on the substrates.

see article for more examples

Key Words

aziridines, tris(dimethylamino)phosphine

ID: J42-Y2017