942275-54-9

Upstream product

• 4248-19-5 tert-butyl carbazate 
• 515-42-4 sodium phenylsulfonate 
• 587-04-2 m-Chlorobenzaldehyde 
• 24424-99-5 di-tert-butyl dicarbonate 
• 873-55-2 sodium benzenesulfonate 

Downstream Products

• 848194-74-1 3-chlorobenzaldehyde N-(tert-butoxycarbonyl)imine 
• 1179345-42-6 C₁₇H₂₂ClNO₆ 
• 1192350-41-6 tert-butyl N-((3-chlorophenyl)(cyano)methyl)carbamate 
• 1214196-70-9 C₈H₈ClNO₂*ClH 
• 1140969-67-0 1-(m-chlorophenyl)-2-nitroethylcarbamic acid t-butyl ester 
• 1242748-83-9 C₁₆H₂₀ClNO₃ 

Relevant academic research and scientific papers

Enantioselective Construction of Sulfur-Containing Tetrasubstituted Stereocenters via Asymmetric Functionalizations of α-Sulfanyl Cyclic Ketones

Asymmetric functionalizations of α-sulfanyl cyclic ketones were realized via chiral phosphoric acid catalyzed enantioselective addition reactions with aldimines, azodicarboxylates and allenamides. A series of chiral organosulfur compounds possessing sulfur-containing tetrasubstituted stereocenters were accessed via these methods, with excellent regioselectivities and high stereoselectivities. (Figure presented.).

Direct Catalytic Asymmetric Mannich-Type Reaction en Route to α-Hydroxy-β-amino Acid Derivatives

A direct catalytic Mannich-type reaction of α-oxygen-functionalized amides was achieved. The use of 7-azaindoline amide was crucial to facilitate direct enolization and subsequent stereoselective addition to imines in a cooperative catalytic system comprising a soft Lewis acid and Br?nsted base. The operationally simple room-temperature protocol furnished a syn-Mannich adduct with high stereoselectivity. Divergent functional group transformation of the amide moiety of the product allowed for expeditious access to enantioenriched syn-configured α-hydroxy-β-amino carboxylic acid derivatives, highlighting the synthetic utility of the present catalysis.

Copper-catalyzed borylative coupling of vinylazaarenes and N-Boc imines

Cu-catalyzed three-component couplings of vinylazaarenes, B2(pin)2, and N-Boc imines are described. Oxidation of the initially formed boronate gives azaarene-containing, Boc-protected amino alcohols with reasonable to good diastereoselectivities.

Enantioselective copper-catalyzed reductive coupling of vinylazaarenes with n -boc aldimines

The diastereo- and enantioselective reductive coupling of vinylazaarenes with N-Boc aldimines is described. The reactions proceed using chiral copper-bisphosphine complexes in the presence of TMDS as a hydride source to give reductive coupling products in moderate to high enantioselectivities.

Disulfonimide-Catalyzed Asymmetric Synthesis of δ-Amino-β-Keto Esters

A chiral disulfonimide-catalyzed asymmetric synthesis of δ-amino-β-keto esters via a vinylogous Mukaiyama-Mannich reaction of the Chan diene with N-Boc imines has been developed. The desired products were obtained in good to excellent yields and enantioselectivities.

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 disulfonimide-catalyzed synthesis of δ-amino-β-ketoester derivatives by vinylogous Mukaiyama-Mannich reactions

An organocatalytic asymmetric synthesis of δ-amino-β-ketoester derivatives has been developed. A chiral disulfonimide (DSI) serves as a highly efficient precatalyst for a vinylogous Mukaiyama-Mannich reaction of readily available dioxinone-derived silylox

Diastereo- and enantioselective Pd(II)-catalyzed additions of 2-alkylazaarenes to N -boc imines and nitroalkenes

A chiral Pd(II)-bis(oxazoline) complex was found to be highly effective in promoting the first direct diastereo- and enantioselective addition of alkylazaarenes to N-Boc aldimines and nitroalkenes under mild conditions. Deprotection of Boc-protected products proceeded readily to provide amines in high yields.

Use of the chiral pool - Practical asymmetric organocatalytic strecker reaction with quinine

An efficient, organocatalytic enantiose-lective synthesis of N-arylsulfonyl α-amino nitriles from the corresponding α-amido sulfones has been developed. This quinine-catalyzed Strecker reaction provides the corresponding cyanated products in good yields a

A novel bis-thiourea organocatalyst for the asymmetric aza-Henry reaction

A novel bis-thiourea/2,2′-diaminobinaphthalene (BINAM)-based catalyst for the asymmetric aza-Henry reaction has been developed. This catalyst promotes the reaction of N-Boc imines with nitroalkanes to afford β-nitroamines with good yields and high enantioselectivities. This catalyst has the advantage that it can be prepared in a single step from commercially available materials. A model is proposed for the catalyst action where both components of the reaction are activated simultaneously by hydrogen bonding. Regardless of the mechanism, the success of the present catalyst demonstrates the potential of bis-thioureas as an interesting class of relatively unexplored catalysts.