Tripeptide-Catalyzed Asymmetric Michael Addition Reaction of β-Nitrostyrenes with Cyclohexanone

Synlett DOI: 10.1055/a-2307-0645 A tripeptide catalyst derived from natural l-amino acids was employed in the reaction of β-nitrostyrenes with cyclohexanone, serving as a model for the asymmetric Michael addition reaction. The reaction was conducted in the presence of H-Pro-Tle-Gly-OH and 2-fluoro-4-chlorobenzoic acid as co-catalysts (each at 20 mol%) in DMF-H2O (5:1) at 0 °C for 3 days. This process yielded the desired Michael adducts with excellent efficiency and good stereoselectivity (up to 98% yield, up to 92% ee). [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents  |  Abstract  |  Full text

Source: Synlett - April 25, 2024 Category: Chemistry Authors: Kippei, Maeda Takeyama, Mitsuki Kohari, Yoshihito Murata, Miki Tags: letter Source Type: research