ISSN:
1573-1111
Keywords:
Asymmetric Michael addition
;
thiol
;
α,β-unsaturated carbonyl compound
;
cyclodextrin complex
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
Abstract The asymmetric Michael addition of aromatic thiols to 2-cyclohexenone and maleic acid esters has been carried out by utilizing their crystalline cyclodextrin complexes suspended in water. The best chiral induction, 30% enantiomeric excess (ee), was achieved in combinations of 2-cyclohexenone and octyl maleate with the crystalline β-cyclodextrin complex of benzenethiol (method A) to afford (S)-3-phenylthiocyclohexanone and (S)-octyl-2-phenylthiosuccinate, respectively, whereas the reaction of benzenethiol with 2-cyclohexenone included in β-cyclodextrin (method B) inversely induced the chiral recognition to give the (R)-adduct with 4–9% ee.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF01153302
