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Synfacts 2010(8): 0949-0949  
DOI: 10.1055/s-0030-1257808
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Aziridination of Cyclic Enones

Contributor(s): Benjamin List, Saihu Liao
F. de Vincentiis, G. Bencivenni, F. Pesciaioli, A. Mazzanti, G. Bartoli, P. Galzerano, P. Melchiorre*
Università di Bologna, Italy; Institute of Chemical Research of Catalonia, Tarragona and Institució Catalana de Recerca i Estudis Avançats, Barcelona, Spain
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Publication History

Publication Date:
22 July 2010 (online)

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Significance

An enantioselective organocatalytic aziridination of cyclic α,β-unsaturated ketones is reported by the authors. In the presence of the catalyst salts A or B and N-Boc-protected nucleophile 2, various cyclic enones 1 of different ring size could be converted into Boc-protected aziridines 3 in good yields and high enantioselectivities. By using the matched combinations of Boc-d-PhgOH/9-epi-NH2-HQ or Boc-l-PhgOH/9-epi-NH2-HQD, both enantiomers of the aziridination products can be obtained.