Synthesis of 1-C-(tetra-O-acetyl-beta-d-galactopyranosyl)-2,3-diiodo-1-propene and its reaction with primary amines.
Iodination of 1-C-(tetra-O-acetyl-beta-d-galactopyranosyl)allene affords an E/Z-mixture of 1-C-(tetra-O-acetyl-beta-d-galactopyranosyl)-2,3-diiodo-1-propene. S(N)2 displacement of the allylic iodide with primary amines affords an E/Z-mixture of allylic amines under a variety of conditions. Due to its experimental simplicity and low cost of reagents, this procedure may find wide use in the laboratory for functionalization of sugar allenes.
Sakee
Uthai
U
Center of Excellence for Innovation in Chemistry, Department of Chemistry, Mahasarakham University, Thailand. uthai.s@msu.ac.th
Nasuk
Chiradet
C
Grigg
Ronald
R
D000466:Alkadienes / Q000138:chemical synthesis* / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D001596:Benzylamines / Q000737:chemistry; D005690:Galactose / Q000737:chemistry; D054879:Halogenation; D015394:Molecular Structure
D000466:Alkadienes; D000588:Amines; D001596:Benzylamines; C025947:propadiene; C030796:benzylamine; D005690:Galactose