Jump to main content
Jump to site search

Issue 38, 2018
Previous Article Next Article

Catalytic enantioselective one-pot approach to cis- and trans-2,3-diaryl substituted 1,5-benzothiazepines

Author affiliations

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.

Graphical abstract: Catalytic enantioselective one-pot approach to cis- and trans-2,3-diaryl substituted 1,5-benzothiazepines

Back to tab navigation

Supplementary files

Publication details

The article was received on 15 Aug 2018, accepted on 12 Sep 2018 and first published on 12 Sep 2018


Article type: Paper
DOI: 10.1039/C8OB01988F
Citation: Org. Biomol. Chem., 2018,16, 6923-6934
  •   Request permissions

    Catalytic enantioselective one-pot approach to cis- and trans-2,3-diaryl substituted 1,5-benzothiazepines

    S. Meninno, I. Quaratesi, C. Volpe, A. Mazzanti and A. Lattanzi, Org. Biomol. Chem., 2018, 16, 6923
    DOI: 10.1039/C8OB01988F

Search articles by author

Spotlight

Advertisements