ol060041l_si_001.pdf (1.86 MB)

Hydroxyalkylation of Conjugated Nitroalkenes with Activated Nonenolizable Carbonyl Compounds

Download (1.86 MB)
journal contribution
posted on 16.03.2006 by Indubhusan Deb, Mamta Dadwal, Shaikh M. Mobin, Irishi N. N. Namboothiri
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 CHCl3 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.