Chemistry Letters, Vol.35, No.4, 358-359, 2006
A facile Zn-mediated stereoselective synthesis of (E)- and (Z)-trisubstituted alkenes from Baylis-Hillman adducts in water and its application
A simple and efficient stereoselective synthesis of (E)- and (Z)-trisubstituted alkenes has been accomplished by treatment of the acetyl derivatives of the Baylis-Hillman adducts with Zn in saturated aq. NH4Cl solution under reflux. The method has been utilized for the preparation of the two chiral insect pheromones, dominicalure-I and dominicalure-II, of the lesser grain borer Rhyzopertha dominica (F).