Effective Ring-Opening Reaction of Aziridines with Trimethylsilyl Compounds:  A Facile Access to β-Amino Acids and 1,2-Diamine Derivatives

Jie Wu, Xue-Long Hou* and Li-Xin Dai

*Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China

J. Wu, X.-L. Hou, L.-X. Dai, J. Org. Chem., 2000, 65, 1344-1348.

DOI: 10.1021/jo9913816

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Abstract

Tetrabutylammonium fluoride promotes ring-opening reactions of aziridines with trimethylsilyl compounds to give the corresponding products regioselectively in excellent yield. This reaction provides a facile and efficient access to cyano-, azido-, or chloroamines. The products are easily transformed to vicinal diamines or β-amino acids.

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Key Words

1,2-aminonitriles, 1,2-azidoamines, 1,2-chloroamines

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ID: J42-Y2000