Terminal Aziridines by Addition of Grignard Reagents or Organoceriums to an (α-Chloro)sulfinylimine
David M. Hodgson*, Johannes Kloesges, Brian Evans
*Department of Chemistry, Chemistry Research Laboratory,
University of Oxford, Mansfield Road, Oxford OX1 3TA, UK, Email: david.hodgson
chem.ox.ac.uk
D. M. Hodgson, J. Kloesges, B. Evans, Synthesis, 2009, 1923-1932.
DOI: 10.1055/s-0029-1216799
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Abstract
Reaction of N-(2-chloroethylidene)-tert-butylsulfinamide with Grignard reagents or organoceriums gives terminal N-tert-butylsulfinyl aziridines in good yields and with organoceriums good diastereomeric ratios. Oxidation of terminal N-tert-butylsulfinyl aziridines provides synthetically useful terminal N-Bus (Bus = tert-butylsulfonyl) aziridines.
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Key Words
aziridines, chiral auxiliaries, imines, nucleophilic addition, organoceriums
ID: J66-Y2009-1780
