685132-82-5

Upstream product

• 79-24-3 Nitroethane 
• 177896-09-2 tert-butyl benzylidenecarbamate 
• 271600-36-3 N-[phenyl(toluene-4-sulfonyl)methyl]tert-butoxycarboxyamide 
• 150884-50-7 benzaldehyde N-boc imine 
• 155396-71-7 tert-butyl N-(phenyl(phenylsulfonyl)methyl)carbamate 
• 4248-19-5 tert-butyl carbazate 
• 100-52-7 benzaldehyde 

Downstream Products

• 198221-75-9 (1R,2S)-1-phenylpropane-1,2-diamine 

Relevant academic research and scientific papers

Dinuclear Zinc-AzePhenol Catalyzed Asymmetric Aza-Henry Reaction of N-Boc Imines and Nitroalkanes under Ambient Conditions

The asymmetric aza-Henry reaction of N-Boc imines and nitroalkanes was realized in the presence of 10 mol % dinuclear zinc-AzePhenol catalysts under ambient conditions. A variety of nitroamines were obtained in good yields (up to 97%) with excellent enantioselectivities (up to 99% ee) and high diasteroselectivity (up to 14:1 dr). Our protocol combined the operational simplicity and mild reaction conditions, thus making the process amenable for technical applications.

Biodegradable Chitosan-Derived Thioureas as Recoverable Supported Organocatalysts – Application to the Stereoselective Aza-Henry Reaction

Eight different biodegradable chitosan-supported bifunctional chiral thioureas have been prepared as a greener and more sustainable alternative to those supported on petrochemical-derived polymers. These organocatalysts promoted an enantioselective aza-He

Enantioselective aza-Henry reaction of: t -Boc protected imines and nitroalkanes with bifunctional squaramide organocatalysts

An organocatalytic asymmetric aza-Henry reaction of t-Boc protected imines with nitroalkanes has been established by chiral acid-base type bifunctional Cinchona alkaloid/squaramide organocatalysts. The cooperation of a quinine motif as a base and sterical

Bottom-up synthesis of supported thioureas and their use in enantioselective solvent-free aza-Henry and Michael additions

Two sets of supported chiral thioureas, which differ in the length of the tether that connects the chiral appendage to the polymer structure and the effective functionalization, have been prepared by copolymerization of styrene, novel styryl thioureas der

Chiral ureas and thioureas supported on polystyrene for enantioselective aza-Henry reactions under solvent-free conditions

Novel bifunctional ureas and thioureas immobilized on sulfonylpolystyrene have been prepared as recoverable and reusable organocatalysts and have been used in the stereoselective aza-Henry reaction under solvent-free conditions. The activity and stereoselection of the catalysts are dependent on the length of the tether bridging the active site and the polymer, the catalyst derived from 1,6-hexane diamine being the best one. It has also been demonstrated that the supported catalysts are more effective than the homologous soluble catalysts.

Asymmetric phase-transfer catalysts bearing multiple hydrogen-bonding donors: Highly efficient catalysts for enantio- and diastereoselective nitro-Mannich reaction of amidosulfones

Bifunctional asymmetric phase-transfer catalysts bearing multiple hydrogen-bonding donors have rarely been explored. The first quaternary ammonium type of these catalysts derived from cinchona alkaloids were readily prepared and found to be highly efficie

Modular bifunctional chiral thioureas as versatile organocatalysts for highly enantioselective aza-Henry reaction and michael addition

A series of new modular bifunctional chiral thiourea organocatalysts were synthesized from natural Cinchona alkaloids and amino acids, and their performance in the aza-Henry reaction of nitroalkanes to imines, the Michael addition of acetylacetone to nitroolefins and the Michael addition of acetone to nitroolefins was investigated. Under the mild conditions, the important building blocks β-nitro amines and γ-nitro carbonyl compounds could be obtained in good yields (up to 95%) with excellent enantioselectivities (up to 99% ee) and diastereoselectivity (up to 17:1). Copyright

A new family of cinchona-derived bifunctional asymmetric phase-transfer catalysts: Application to the enantio- and diastereoselective nitro-Mannich reaction of amidosulfones

A new family of bifunctional H-bond donor phase-transfer catalysts derived from cinchona alkaloids has been developed and evaluated in the enantio- and diastereoselective nitro-Mannich reaction of in situ generated N-Boc-protected imines of aliphatic, aromatic, and heteroaromatic aldehydes. Under optimal conditions, good reactivity and high diastereoselectivities (up to 24:1 dr) and enantioselectivities (up to 95% ee) were obtained using a 9-amino-9- deoxyepiquinidine-derived phase-transfer catalyst possessing a 3,5-bis(trifluoromethyl)phenylurea H-bond donor group at the 9-position.

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.