Sequential knoevenagel reaction/Mislow-Evans rearrangement catalyzed by heterogeneous amine grafted on silica in water, leading to gamma-hydroxy-alpha,beta-unsaturated nitrile

摘要

gamma-Hydroxy-alpha,beta -unsaturated nitrile was obtained by the reaction of alpha-arylsulfinylacetonitrile with aldehyde in water, which was catalyzed by N,N-diethylaminopropylated silica gel. The overall transformation proceeded via five sequential reactions, 1,2-addition of acetonitrile, dehydration (Knoevenagel condensation), isomerization of the double bond, rearrangement of sulfinyl group (Mislow-Evans rearrangement) and hydrolysis of sulfinyl ester. The reaction condition was mild such that the AcO, TBMDSO or OTHP group remained intact in the products.