A highly stereoselective and recyclable microgel-supported bifunctional sulfonamide organocatalyst for asymmetric alcoholysis of meso-cyclic anhydrides: a thermo-responsive “organic nanoreactor”

Abstract

A novel thermosensitive bifunctional sulfonamide microgels catalyst was synthesized by immobilization on a highly cross-linked three-dimensional network structure through covalent interactions. The microgels-supported organocatalyst has been successfully applied to catalyze...

Bifunctional Sulfonamide as Hydrogen Bonding Catalyst in Catalytic Asymmetric Reactions: Concept and Application in the Past Decade

“…Inspired by Rueping's successful work, our group also developed novel microgel-supported sulfonamide organocatalyst with the same chiral structure as 39. [84] Slightly higher ee value (90 % ee) but lower recyclability was obtained in our work compared to Rueping's work.…”

“…This supported sulfonamide was utilized in the synthesis of Roche lactone, which is the key intermediate of natural vitamin (+)‐biotin, however, 120 mol % of catalyst 42 was necessary. Inspired by Rueping's successful work, our group also developed novel microgel‐supported sulfonamide organocatalyst with the same chiral structure as 39 [84] . Slightly higher ee value (90 % ee) but lower recyclability was obtained in our work compared to Rueping's work.…”

“…Inspired by good recyclability of heterogeneous catalysts, most reports after 2011 focused on immobilization or polymerization of quinine sulfonamide for improving application value of sulfonamide catalysis in desymmetric reaction [79–84] . In this context, Connon and coworkers applied the magnetic nanoparticles (MNPs) as catalyst support for the cinchona alkaloid derived sulfonamide catalyst in 2011 (Scheme 32).…”

“…Inspired by good recyclability of heterogeneous catalysts, most reports after 2011 focused on immobilization or polymerization of quinine sulfonamide for improving application value of sulfonamide catalysis in desymmetric reaction. [79][80][81][82][83][84] In this context, Connon and coworkers applied the magnetic nanoparticles (MNPs) as catalyst support for the cinchona alkaloid derived sulfonamide catalyst in 2011 (Scheme 32). [79] MNPssupported sulfonamide 40 could catalyze methanolysis of cyclic anhydrides effectively though lower enantioselectivity was obtained compared to its corresponding homogeneous catalyst.…”

Design, synthesis and application of a magnetic H-bond catalyst in the preparation of new nicotinonitriles via cooperative vinylogous anomeric-based oxidation

“…18,19 There are different types of hydrogen bonding catalysts, including organic compounds, metal complexes, enzymes, and even some solid materials. [20][21][22] Nicotinonitriles are a class of organic compounds that contain a nitrile group (-CN) attached to the pyridine ring of nicotine. 23 Various nicotinonitriles that have medicinal and biological properties have been introduced in recent years.…”