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Synfacts 2008(10): 1101-1101  
DOI: 10.1055/s-2008-1078146
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Stereoselective Aziridine Alkylation Reactions

Contributor(s): Benjamin List, Steffen Müller
T. A. Moss, D. R. Fenwick, D. J. Dixon*
The University of Manchester and Pfizer Global Research & Development, Sandwich, UK
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Publication History

Publication Date:
22 September 2008 (online)

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Significance

A new stereoselective access to γ-amino butyric acid derivatives via enantioselective ring-opening reactions of aziridines is reported. The treatment of different substituted indanones with o-(trifluoromethane)benzenesulfonyl aziridines in the presence of catalyst 1 gave the desired products in good yields and excellent enantioselectivities. The use of enantiomerically pure aziridines as alkylating agents was also investigated. Here, the same catalyst provided good results for different substrates, for example, indanones, cyclopenta­nones, tetralones, lactams and succinimides, regarding yields and diastereoselectivities.