American Chemical Society
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Olefination of α-Hydroxy or α-Aminoaldehyde Derivatives via Reaction of Their Arylsulfonylhydrazones with Sulfonyl Anions

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journal contribution
posted on 2004-08-20, 00:00 authored by Jerzy Wicha, Andrzej Zarecki
Reaction of tosylhydrazones of O-substituted α-hydroxy or N-substituted α-amino aldehydes (2, 7, 11, 15, 17, and 20) with selected α-magnesio alkyl phenyl sulfones afforded the respective derivatives of allylic alcohols or allylic amines. 2,3-O-Isopropylidene-d-glyceraldehyde (1) was transformed into its tosylhydrazone (2) and then olefins 4a with retention of optical purity.