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

✍ Scribed by Zdeněk Wimmer; David Šaman; Jelena Kuldová; Didier Desmaële; Jean d'Angelo; Françoise Goudey-Perrière

• Publisher: John Wiley and Sons
• Year: 1998
• Tongue: German
• Weight: 121 KB
• Volume: 81
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/(sici)1522-2675(19981111)81:11<2017::aid-hlca2017>3.0.co;2-p

✦ Synopsis

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 2substituted 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.