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Highly Efficient Asymmetric Trans-Selective Aziridination of Diazoacetamides and N-Boc-imines Catalyzed by Chiral Brønsted Acids

Xiaofei Zeng, Xin Zeng, Zhenjiang Xu, Min Lu and Guofu Zhong*

*Division of Chemistry & Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, 21 Nanyang link, Singapore 637371, Singapore, Email: guofuntu.edu.sg

X. Zeng, X. Zeng, Z. Xu, M. Lu, G. Zhoung, Org. Lett., 2009, 11, 3036-3039.

DOI: 10.1021/ol901047w (free Supporting Information)


Abstract

A clean and fast aziridination of diazoacetamides with N-Boc-imines, as well as N-Cbz-imines, catalyzed by a chiral phosphoric acid in DCM at room temperature achieves excellent yields, diastereoselectivities, chemoselectivities, and enantioselectivities.

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Key Words

Aziridines, Organocatalysis


ID: J54-Y2009-2130