One-Pot Stereoselective Synthesis of anti 3-Alkyl and 3-Aryl-N-p-tosyl-aziridine-2-ketones and 3-Aryl-N-p-tosyl-aziridine-2-carboxylates

Dianjun Chen, Cody Timmons, Li Guo, Xin Xu, Guigen Li*

*Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, TX 79409-1061, USA, Email: guigen.littu.edu

D. Chen, C. Timmons, L. Guo, X. Xu, G. Li, Synthesis, 2004, 2479-2484.

DOI: 10.1055/s-2004-831203

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Abstract

An efficient and practical aminohalogenation and in situ intramolecular S_N2 substitution of α,β-unsaturated esters and ketones gave N-p-tosyl-aziridine-2-ketones and carboxylates in moderate to good yields and excellent anti stereoselectivity. Triethylamine was found to be an effective base for the in situ cyclization for most substrates.

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Key Words

aziridination, aminohalogenation, haloamines, cinnamates, enones

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ID: J66-Y2004-2340