Dramatic rate acceleration of the Baylis-Hillman reaction in homogeneous medium in the presence of water.
[reaction: see text] In homogeneous H(2)O/solvent medium, the reaction rate of aromatic aldehydes and acrylonitrile or acrylate was greatly accelerated, which led to shorter reaction time, lower reaction temperature, and higher yield. In this reaction, Me(3)N, DMAP, DABCO, and urotropine were good catalysts. Except for low-carbon alcohols, tetrahydrofuran, 1,4-dioxane, and acetonitrile could be chosen as the solvent. Under this condition, the diastereoselective reaction of nitrobenzaldehyde and L-menthyl acrylate was realized with 88-99% de.
Cai
Juexiao
J
State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, People's Republic of China.
Zhou
Zhenghong
Z
Zhao
Guofeng
G
Tang
Chuchi
C