TheMichael-Type Addition Reaction: A Stereocontrolled Construction of a New Quaternary Chiral Center at C(2) of 2-(4-Hydroxybenzyl)cyclohexanone Derivatives

Abstract

The Michael-type addition reaction was used as a convenient method for the stereocontrolled construction of a new quaternary C-center at position 2 of 2-substituted cyclohexanones (Scheme) with the aim to study the effect of an additional substituent at C(2) in a series of biologically active compounds bearing generally a 2-substituted cyclohexanone moiety. Thus, a new series of compounds consisting of a racemate (RS)-12 and its enantiomers (S)- and (R)-12 (ee ≥96% for both enantiomers) was obtained. The Michael adduct derivatives (S)-, (R)-, and (RS)-12 were subjected to a biological screening using several non-related insect species.