A solvent-dependent chirality-switchable thia-Michael addition to α,β-unsaturated carboxylic acids using a chiral
Noboru Hayama1,2, Yusuke Kobayashi1, Eriko Sekimoto2
1Graduate School of Pharmaceutical Sciences , Kyoto University , Yoshida, Sakyo-ku , Kyoto 606-8501 , Japan .
Abstract:
An asymmetric thia-Michael addition of arylthiols to α,β-unsaturated carboxylic acids using a thiourea catalyst that bears arylboronic acid and tertiary amine moieties is reported. Both enantiomers of the Michael adducts can be obtained in high enantioselectivity and good yield merely by changing the solvent. The origin of the chirality switch in the products was examined in each solvent via spectroscopic analyses.
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