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: clums.xjb.ac.cn, xuyjms.xjb.ac.cn

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

DOI: 10.1021/acs.joc.6b02669

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Abstract

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.

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Key Words

aziridines, tris(dimethylamino)phosphine

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ID: J42-Y2017