Asymmetric Michael addition of 4H-thiopyran-4-one to nitroolefins catalyzed by diamine mono-N-sulfonamide and its application to concise synthesis of enantiopure multiring heterocycles

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

“…Asymmetric Michael addition of nitroolefins as Michael acceptors was also reported by Yao and coworkers, who used heteroatom cyclohexanone system as Michael donor (Scheme 14). [45] The novel sulfonamide 22 with C 2 ‐symmetrical 2,2’‐bipyrrolidine moiety was developed to catalyze the Michael addition of 4 H ‐thiopyran‐4‐one to a series of nitroolefins with excellent enantio‐ (up to 98 %) and almost perfect diastereo‐selectivity (99 : 1 dr), which was superior to 20 in the same process. A proposed catalytic mode of 22 was also presented in Yao's work, which held the idea that the sulfonamide moiety worked as a H‐bonding acceptor could be a successful protocol to activate the nitroolefins in Michael reactions.…”

Research Progress on Application of Organic Diamines and Their Derivatives

“…An organic diamine was synthesized and evaluated as a catalyst in Machel addition reaction by Mo et al, which was identified to exhibit better catalytic ability than the traditional chiral pyrrolidine catalysts in higher chemical yields [33] (Scheme 7).…”

An amphiphilic organic catalyst for the direct asymmetric Michael addition of cycloketone to nitroolefins in water

“…The Michael addition is one of the most powerful methods for the formation of C-C bonds in organic synthesis [1]. Since List et al [2] reported the proline-catalyzed asymmetric Michael addition reaction, the direct asymmetric Michael addition of unmodified carbonyl compounds into nitro olefins has been regarded as an efficient synthesis route for chiral γ-nitro carbonyl compounds [3][4][5][6][7], which serve as versatile building blocks for the synthesis of complex organic molecules [8,9]. Meanwhile, effective organocatalytic Michael addition reactions in an aqueous system have also been reported by several research groups [10][11][12].…”