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Synlett 2001; 2001(6): 0839-0841
DOI: 10.1055/s-2001-14607
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Aziridination of 5-Methyl-4H-1,3-dioxins by N-Tosyliminophenyliodinane: A One-step Procedure for the Synthesis of α-Methylserinal Derivatives

Susanne Flock* , Herbert Frauenrath
  • *Universität Gh Kassel, Fachbereich 19 - Biologie/Chemie, Heinrich-Plett-Str. 40, 34109 Kassel, Germany; Fax + 49 (0)561-8 04 46 49; E-mail: frauenra@hrz.uni-kassel.de
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Publication Date:
31 December 2001 (online)

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The methyl analogue of Garner's aldehyde, N-tosyl-4-methyl-N,O-isobutyrylideneserinal, has been prepared in a one-step reaction by CuClO4-catalyzed aziridination of 2-isopropyl-5-methyl-4H-1,3-dioxin with N-tosyliminophenyliodinane and transformed into α-methylserine derivatives, e.g. α-vinylalanine.

amino aldehydes - aziridination - rearrangements - α-alkyl-α-amino acids - 4H-1,3-dioxins

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