479423-27-3

Upstream product

• 4248-19-5 tert-butyl carbazate 
• 873-55-2 sodium benzenesulfonate 
• 104-87-0 4-methyl-benzaldehyde 
• 24424-99-5 di-tert-butyl dicarbonate 
• 515-42-4 sodium phenylsulfonate 

Downstream Products

• 1000693-81-1 (R)-N-tert-butyloxycarbonyl-α-(4-methylphenyl)benzylamine 
• 1000693-89-9 (S)-N-tert-butyloxycarbonyl-α-(4-methylphenyl)benzylamine 
• 1159542-00-3 C₁₄H₂₁NO₃ 
• 1192350-30-3 C₁₄H₁₈N₂O₂ 
• 1204704-98-2 (S)-tert-butyl (cyano(4-methylphenyl)methyl)carbamate 
• 134722-06-8 (4-methylphenyl)-glycine hydrochloride 
• 1226894-14-9 methyl (2R,3S)-3-(tert-butoxycarbonylamino)-2-(diphenylmethyleneamino)-3-p-tolylpropanoate 
• 1237534-80-3 tert-butyl [(6-hydroxybenzo[d][1,3]dioxol-5-yl)(p-tolyl)methyl]carbamate 
• 1273585-67-3 methyl 2-(tert-butoxycarbonylamino)-2-(4-methylphenyl)acetate 
• 120157-93-9 N-(tert-butyloxycarbonyl)-4-methylbenzylamine 
• 28044-77-1 [(tert-butoxycarbonyl)amino](4-methylphenyl)acetic acid 
• 1262642-57-8 N-tert-butyl ((2-(pyridin-2-yl)phenyl)(p-tolyl)methyl)carbamate 
• 1309658-00-1 (2S,3R)-3-[N-(t-butoxycarbonyl)-2-methyl-3-(4-methylphenyl)aziridine-2-carbonyl]-oxazolidin-2-one 
• 1309658-17-0 (2R,3S)-3-[N-(t-butoxycarbonyl)-2-methyl-3-(4-methylphenyl)aziridine-2-carbonyl]-oxazolidin-2-one 

Relevant academic research and scientific papers

Nanoceria as an efficient and green catalyst for the chemoselective N-tert-butyloxycarbonylation of amines under the solvent-free conditions

Nanocerium oxide mediated an efficient and green protocol has been described for the chemoselective N-tert-butyloxycarbonylation of amines under the solvent-free conditions at ambient temperature. Various aliphatic, aromatic and heteroaromatic amines were protected using developed protocol and several functional groups such as alcohol, phenol and ester were well tolerated under these conditions. The rapid reaction rate, mild conditions, very good functional group tolerance, excellent yield, solvent-free, easy recovery products and excellent catalyst recyclability are the advantages of this protocol. This makes the protocol feasible, economical and environmentally benign.

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.).

Two Distinct Ag(I)- And Au(I)-Catalyzed Olefinations between α-Diazo Esters and N-Boc-Derived Imines

Metal-catalyzed reactions between α-diazo esters and imines were well-known to yield aziridine derivatives exclusively. This work reports two new olefination reactions between N-Boc-derived (Boc = tert-Butyloxycarbonyl) imines and α-diazo esters with Ag(I) and Au(I) catalysts, respectively. Our mechanistic studies reveal that these new olefinations involve an initial attack of diazo esters on metal/imine complexes to form Mannich-addition intermediates, which subsequently afford α-aryl-β-aminoacrylates via a Roskamp reaction, or to form β-aryl-β-aminoacrylates via the formation of silver carbenes.

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.

Asymmetric Aminalization via Cation-Binding Catalysis

Asymmetric cation-binding catalysis, in principle, can generate “chiral” anionic nucleophiles, where the counter cations are coordinated within chiral environments. Nitrogen nucleophiles are intrinsically basic, therefore, its use as nucleophiles is often challenging and limiting the scope of the reaction. Particularly, a formation of configurationally labile aminal centers with alkyl substituents has been a formidable challenge due to the enamine/imine equilibrium of electrophilic substrates. Herein, we report enantioselective nucleophilic addition reactions of potassium phthalimides to Boc-protected alkyl- and aryl-substituted α-amido sulfones. In situ generated imines smoothly reacted with the nitrogen nucleophiles to corresponding aminals with good to excellent enantioselectivitiy under mild reaction conditions. In addition, transformation of aminal products gave biologically relevant pyrrolidinone-fused hexahydropyrimidine scaffold with excellent stereoselectivity and good yield.

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.

Efficient synthesis of α-(N-Boc)aminoamides by addition of a carbamoylsilane to N-Boc-imines

N,N-Dimethylcarbamoyl(trimethyl)silane reacted with N-Boc-imines in anhydrous benzene under catalysts-free conditions to afford N-Boc-protected α-amino amides in good yields (72-89%). The electronic property and the steric hindrance of substituent on the N-Boc-imines affected the reaction.

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.

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.

Copper(I)-Catalyzed Asymmetric Pinacolboryl Addition of N-Boc-imines Using a Chiral Sulfoxide - Phosphine Ligand

Highly efficient and enantioselective copper(I)-catalyzed pinacolboryl addition of N-Boc-imines is reported. By using a single chiral sulfoxide-(dialkyl)phosphine (SOP) ligand, both enantiomeric isomers of α-amino boronic esters were obtained through an achiral counteranion switch.