SYNTHESIS OF 4-SUBSTITUTED CHIRAL CHROMANOLS BY USING MALONIC ESTER AND O-HYDROXYAROMATIC α,β-UNSATURATED ALDEHYDES

摘要

PURPOSE: A method for preparing chiral chromanol in which 4th site is substituted is provided to show high yield and enantioselectivity by comprising the step of selecting malonate as a nucleophilic agent and diphenylprolinol TMS as an organic catalyst. CONSTITUTION: A method for preparing chroman-2-ol with an optical activity, in which 4th site is substituted comprises the step of conjugate addition of malonate to ortho-hydroxycinnamaldehyde under the presence of a diphenylprolinol TMS ether catalyst. Malonate and ortho-hydroxyciannamaldehyde are denoted by chemical formulas 1 and 2, respectively. The catalytic reaction is performed in one or more solvents selected among dichloromethane, toluene, methanol, and chloroform.