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Multicomponent reactions in chiral ionic liquids: A stereocontrolled route to mercaptopyranothiazoles

✍ Scribed by Lal Dhar S. Yadav; Beerendra S. Yadav; Vijai K. Rai

Publisher
Journal of Heterocyclic Chemistry
Year
2008
Tongue
English
Weight
325 KB
Volume
45
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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A low hazardous, one‐pot, expeditious annulation involving tandem Knoevenagel, Michael and ring transformation reactions of 3‐arylrhodanines, aromatic aldehydes and a mercaptoacetyl transfer agent, 2‐methyl‐2‐phenyl‐1,3‐oxathiolan‐5‐one, diastereoselectively yields 6‐mercaptopyranothiazoles. The annulation is performed using a chiral ionic liquid (Pro~2~SO~4~) as the reaction medium and catalyst, and proceeds via an isolable intermediate.

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## Abstract A novel chiral ionic liquid, compound **1**, based on camphorsulfonic acid, was prepared. A catalytic amount of **1** readily promotes L‐proline‐catalyzed aldol reactions, with good chemoselectivity, both in H~2~O and in organic solvents. Further, the aldol reaction of cyclohexanone wit