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The Michael ‐Type Addition Reaction: A Stereocontrolled Construction of a New Quaternary Chiral Center at C(2) of 2‐(4‐Hydroxybenzyl)cyclohexanone Derivatives
Author(s) -
Wimmer Zdeněk,
Šaman David,
Kuldová Jelena,
Desmaële Didier,
d'Angelo Jean,
GoudeyPerrière Françoise
Publication year - 1998
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/(sici)1522-2675(19981111)81:11<2017::aid-hlca2017>3.0.co;2-p
Subject(s) - chemistry , cyclohexanone , moiety , enantiomer , adduct , substituent , stereochemistry , michael reaction , chirality (physics) , organic chemistry , catalysis , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark
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.