Stereoselective Synthesis of Polyfunctionalized Nitrothianes: Enhancement of Stereoselectivity by Microwaves

Abstract The Michael addition of nitromethane to (Z,Z)-2,2′-thiobis(1,3-diarylprop-2-en-1-ones) in the presence of NaOEt in dimethylformamide (DMF)/alcohol under thermal conditions affords a diastereomeric mixture of 2a,6e-diaroyl-3a,5e-diaryl-4e-nitrothianes and 2e,6e-diaroyl-3e,5e-diaryl-4e-nitrothianes with a dr of ∼3:1/4:1 respectively. This reaction under microwave irradiation in DMF/alcohol afforded solely 2a,6e-diaroyl-3a,5e-diaryl-4e-nitrothianes, disclosing enhancement of stereoselectivity by microwaves. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications® to view the free supplemental file.