39220-93-4Relevant articles and documents
Nitronate anion recognition and modulation of ambident reactivity by hydrogen-bonding receptors
Linton, Brian R.,Goodman, M. Scott,Hamilton, Andrew D.
, p. 2449 - 2455 (2000)
Nitronate anions were shown to form complexes in DMSO with hydrogen-bonding receptors such as 1,3-dimethylthiourea 1 (Ka = 120M-1) and bicyclic guanidinium2 (Ka = 3200M-1). A ditopic bis-thiourea exhibited increased association with substrates, that contained either two nitronates (Ka = 7000M-1) or a combination of nitronate and carboxylate (Ka = 1200M-1). Complexation of nitronate resulted in a change in the ambident reactivity during alkylation with p-nitrobenzyl bromide. The predominant reaction pathway was shifted from oxygen alkylation to carbon alkylation as receptor binding strength increased. Kinetic analysis indicated an overall inhibition of nitronate reactivity, and this suggests that greater suppression of the oxygen pathway allows carbon alkylation to predominate.
Ethyl acrylate conjugated polystyryl-diphenylphosphine - An extremely efficient catalyst for Henry reaction under solvent-free conditions (SolFC)
Rokhum, Lalthazuala,Bez, Ghanashyam
, p. 300 - 306 (2013/06/05)
Over the last few decades, the fast-growing development of polymer supported reagents has led to the synthesis of a variety of reagents on solid support. Some of the major advantages of using such reagents are that they are less hygroscopic, easy to recover, and can be recycled. Here, we have demonstrated that in situ generated ethyl acrylate conjugated polystyryl-diphenylphosphine (PDPP-EA) derived from the reaction of a mixture of polystyryl-diphenylphosphine and ethyl acrylate in a stoichiometric ratio can efficiently catalyze the synthesis of β-nitroalcohols from the reaction of aldehydes and nitroalkanes under solvent-free conditions (SolFC).
Direct asymmetric dynamic kinetic resolution by combined lipase catalysis and nitroaldol (Henry) reaction
Vongvilai, Pornrapee,Larsson, Rikard,Ramstroem, Olof
supporting information; experimental part, p. 448 - 452 (2009/04/10)
The asymmetric synthesis of β-nitroalkanol derivatives was simply achieved by a combined nitroaldol (Henry) reaction with lipase-catalyzed transesterification in high yield and enantiomeric purity (up to 92% and 99% ee) through a direct one-pot procedure.