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Synthesis 2009(11): 1923-1932
DOI: 10.1055/s-0029-1216799
DOI: 10.1055/s-0029-1216799
FEATUREARTICLE
© Georg Thieme Verlag
Stuttgart ˙ New York
Terminal Aziridines by Addition of Grignard Reagents or Organoceriums to an (α-Chloro)sulfinylimine
Further Information
Received
29 March 2009
Publication Date:
12 May 2009 (online)
Publication History
Publication Date:
12 May 2009 (online)
Abstract
Reaction of N-(2-chloroethylidene)-tert-butylsulfinamide with Grignard reagents or organoceriums gives terminal N-tert-butylsulfinyl aziridines in good yields and (mainly with organoceriums) good diastereomeric ratios. Oxidation of terminal N-tert-butylsulfinyl aziridines provides synthetically useful terminal N-Bus (Bus = tert-butylsulfonyl) aziridines.
Key words
aziridines - chiral auxiliaries - imines - nucleophilic addition - organoceriums
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References
CCDC 712180, available at http://www.ccdc.cam.ac.uk.
26Crimmins and Shamszad observed reaction of mesitylMgBr with a tert-butylsulfinyl aldimine bearing a (more strongly coordinating) α-PMBO group proceeded with the sense of asymmetric induction expected for an α-coordinating group (ref. 23).
30CCDC 683080, available at http://www.ccdc.cam.ac.uk.
36The principal authors of refs. 32 and 35 have accepted that their published data for material obtained on deprotection is not consistent with that expected for the deprotected aziridines (personal communications with Profs. Stockman and Aggarwal).