Hydroxyalkylation of conjugated nitroalkenes with activated nonenolizable carbonyl compounds.
[reaction: see text] The Morita-Baylis-Hillman reaction of a variety of conjugated nitroalkenes with activated nonenolizable carbonyl compounds such as glyoxylate, trifluoropyruvate, pyruvaldehyde, and ninhydrin in the presence of 40-100 mol % of DMAP in acetonitrile or 100 mol % of imidazole in CHCl(3) or THF provided the adducts in decent to good yields. In most cases, the reactions catalyzed by DMAP in acetonitrile were faster and provided the desired MBH adducts in higher yields as compared to the imidazole catalyzed reactions.
Deb
Indubhusan
I
Department of Chemistry, Indian Institute of Technology, Bombay, Mumbai 400 076, India.
Dadwal
Mamta
M
Mobin
Shaikh M
SM
Namboothiri
Irishi N N
IN