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Synthesis 2005(12): 2022-2028  
DOI: 10.1055/s-2005-869976
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Asymmetric N-Arylaziridine Derivatives Using a New Chiral Phase-Transfer Catalyst

Eagambaram Murugan*a, Ayyanar Sivab
a Department of Physical Chemistry, School of Chemical Sciences, University of Madras, Guindy campus, Chennai-600 025, TN, India
Fax: +91(44)22352494; e-Mail: murugan_e68@yahoo.com;
b Department of Chemistry, Gandhigram Rural Institute-Deemed University, Gandhigram-624 302, TN, India
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Publikationsverlauf

Received 7 January 2005
Publikationsdatum:
24. Juni 2005 (online)

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Abstract

Substituted N-arylaziridine derivatives were synthesized in an enantioselective manner from N-acyl-N-arylhydroxylamine and electron deficient olefins using chiral phase-transfer catalysts (CPTCs) derived from cinchona alkaloids. The structures of the CPTCs were ascertained through various spectral techniques such as FT-IR, 1H NMR, 13C NMR, and mass spectroscopy, as well as elemental analyses. The efficiency and chiral behavior of a range of CPTCs were studied with respect to both yield and ee. The chemical yields were in the range of 24-92% and ee was 29-95%. It was observed that the S-enantiomers were more predominant than the R-enantiomers with cinchonidine as catalyst; whereas the R-enantio­mers were more predominant in the case of cinchonine based CPTC. We propose here a suitable mechanism for the formation of chiral aziridines as well as optimized procedures for a range of N-arylaziridine derivatives.

Key words

enantioselection - cinchona alkaloid - aziridine - hydroxamic acids - electron deficient olefins