A first one-pot synthesis, isomerization and synthetic utility of mono- and bis Morita-Baylis-Hillman adducts of 1,1′-ferrocenedialdehyde

A one-pot synthesis of mono- and bis-Morita-Baylis-Hillman adducts of 1,1′-ferrocenedialdehyde has been achieved. These adducts undergo a facile and efficient stereoselective isomerization with a number of saturated, unsaturated, aromatic alcohols, phenols and thiophenol with a montmorillonite K10 clay catalyst to afford highly functionalized trisubstituted alkene derivatives of ferrocene. The synthetic utility of isomerized derivatives has been demonstrated by a ferrocene appended novel macrocycle synthesis, a ferrocenyl bis-triazole synthesis and an evaluation of the liquid crystalline property of a cholesterol derivative of ferrocene.

a. CH2CHCN, DABCO, RT, 6h; b. ROH, mont.K10 clay, heat, 12h; c. Cu(OAc)2, MeOH-Py., Reflux, 1 h; d. CuCl2, Acetone, O2, RT, 5h.