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Relevant academic research and scientific papers

Heterobimetallic transition metal/rare earth metal bifunctional catalysis: A Cu/Sm/schiff base complex for Syn -selective catalytic asymmetric nitro-mannich reaction

The full details of a catalytic asymmetric syn-selective nitro-Mannich reaction promoted by heterobimetallic Cu/Sm/dinucleating Schiff base complexes are described, demonstrating the effectiveness of the heterobimetallic transition metal/rare earth metal bifunctional catalysis. The first-generation system prepared from Cu(OAc)2/Sm(O-iPr)3/Schiff base 1a = 1:1:1 with an achiral phenol additive was partially successful for achieving the syn-selective catalytic asymmetric nitro-Mannich reaction. The substrate scope and limitations of the first-generation system remained problematic. After mechanistic studies on the catalyst prepared from Sm(O-iPr)3, we reoptimized the catalyst preparation method, and a catalyst derived from Sm 5O(O-iPr)13 showed broader substrate generality as well as higher reactivity and stereoselectivity compared to Sm(O-iPr)3. The optimal system with Sm5O(O-iPr)13 was applicable to various aromatic, heteroaromatic, and isomerizable aliphatic N-Boc imines, giving products in 66-99% ee and syn/anti = >20:1-13:1. Catalytic asymmetric synthesis of nemonapride is also demonstrated using the catalyst derived from Sm5O(O-iPr)13.

Catalytic asymmetric nitro-Mannich reactions with a Yb/K heterobimetallic catalyst

A catalytic asymmetric nitro-Mannich (aza-Henry) reaction with rare earth metal/alkali metal heterobimetallic catalysts is described. A Yb/K heterobimetallic catalyst assembled by an amide-based ligand promoted the asymmetric nitro-Mannich reaction to afford enantioenriched anti-β- nitroamines in up to 86% ee. Facile reduction of the nitro functionality allowed for efficient access to optically active 1,2-diamines.

Doubly stereocontrolled asymmetric aza-henry reaction with in situ generation of n-boc-imines catalyzed by novel rosin-derived amine thiourea catalysts

The doubly stereocontrolled organocatalytic aza-Henry reaction of nitroalkanes to N-Bocimines generated in situ from a variety of substituted α-amido sulfones was investigated for the first time, in general, affording the corresponding products with high

syn-selective catalytic asymmetric nitro-Mannich reactions using a heterobimetallic Cu-Sm-Schiff base complex

syn-Selective catalytic asymmetric nitro-Mannich reactions using a heterobimetallic Cu/Sm/Schiff base complex are described. The present method is complementary to the previously reported methods, and products were obtained in high syn-selectivity (>20:1)

Highly enantioselective thiourea-catalyzed nitro-mannich reactions

(Chemical Equation Presented) Approaching "privileged" status? A new and highly effective enantioselective catalyst for the nitro-Mannich reaction was identified by modification of thioureabased Strecker catalysts (see scheme). Products are obtained in hi