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Catalytic enantioselective one-pot approach to cis- and trans-2,3-diaryl substituted 1,5-benzothiazepines
Sara Meninno1, Ilaria Quaratesi, Chiara Volpe
1Dipartimento di Chimica e Biologia "A. Zambelli", Università di Salerno, Via Giovanni Paolo II 132, I-84084, Fisciano, Italy. lattanzi@unisa.it smeninno@unisa.it.
Abstract:
The first enantioselective catalytic approach to cis- and trans-2,3-diaryl substituted 1,5-benzothiazepines has been conveniently developed in a one-pot fashion, starting from α,β-unsaturated acyl pyrazoles and 2-aminothiophenol. The organocatalytic two-step sulfa-Michael/lactamization sequence is promoted by a readily available bifunctional thiourea and p-toluenesulfonic acid, respectively. The protocol enables access to both N-unprotected cis- and trans-diastereoisomers in moderate to satisfactory overall yields (up to 84%) and good to excellent ee values (up to 99%). Mechanistic investigations helped to shed light on the regio- and stereoselective outcome of the process.
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