Olefination of alpha-hydroxy or alpha-aminoaldehyde derivatives via reaction of their arylsulfonylhydrazones with sulfonyl anions.
Reaction of tosylhydrazones of O-substituted alpha-hydroxy or N-substituted alpha-amino aldehydes (2, 7, 11, 15, 17, and 20) with selected alpha-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.
Institute of Organic Chemistry, Polish Academy of Sciences, ul. Kasprzaka 44, 01-224 Warsaw, Poland. jwicha@icho.edu.pl
Jerzy
J
Wicha
Andrzej
A
Zarecki