Files
Document type
ArticleVersion
Published versionPublication date
Publication license
Please use this identifier to cite or link to this item: https://hdl.handle.net/2445/208601
Direct, stereodivergent, and catalytic Michael additions of thioimides to α,β-unsaturated aldehydes – Total synthesis of Tapentadol
Journal Title
Director/Tutor
Journal ISSN
Volume Title
Related resource
Abstract
Direct and stereodivergent Michael additions of N-acyl 1,3-thiazinane-2-thiones to α,β-unsaturated aldehydes catalyzed by chiral nickel(II) complexes are reported. The reactions proceed with a remarkable regio-, diastereo-, and enantioselectivity, so access to any of the four potential Michael stereoisomers is granted through the appropriate choice of the chiral ligand of the nickel(II) complex. Simple removal of the heterocyclic scaffold furnishes a wide array of either syn or anti enantiomerically pure derivatives, which can be exploited for the asymmetric synthesis of biologically active compounds, as demonstrated in a new approach to tapentadol. In turn, a mechanism, based on theoretical calculations, is proposed to account for the stereochemical outcome of these transformations.
Subject
Subject (English)
Citation
Citation
GALEOTE, Oriol, et al. Direct, stereodivergent, and catalytic Michael additions of thioimides to α,β-unsaturated aldehydes – Total synthesis of Tapentadol. Angewandte Chemie-International Edition. 2024. Vol. 63, num. e202319308. ISSN 1433-7851. [consulted: 8 of August of 2026]. Available at: https://hdl.handle.net/2445/208601