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

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 int...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2004-08, Vol.69 (17), p.5810-5812
Main Authors: Wicha, Jerzy, Zarecki, Andrzej
Format: Article
Language:English
Subjects:
Aliphatic compounds
Chemistry
Exact sciences and technology
Organic chemistry
Preparations and properties
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0499118