177723-19-2

Upstream product

• 74-90-8 hydrogen cyanide 
• 177896-09-2 tert-butyl benzylidenecarbamate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 48108-77-6 (S)-α-phenylglycinenitrile 
• 143978-92-1 Boc-L-Phg-NH₂ 
• 155396-71-7 tert-butyl N-(phenyl(phenylsulfonyl)methyl)carbamate 
• 7677-24-9 trimethylsilyl cyanide 
• 150884-50-7 benzaldehyde N-boc imine 
• 1236163-01-1 C₃₂H₂₉N₄OP 
• 1310539-57-1 C₂₀H₃₁N₄OP 
• 1186139-42-3 C₁₉H₃₀N₃OP 
• 407-25-0 trifluoroacetic anhydride 

Downstream Products

• 1120367-22-7 C₁₃H₁₇N₅O₂ 
• 2935-35-5 (S)-2-phenylglycine 
• 137102-30-8 (S)-N₁-tert-butoxycarbonyl-1-phenyl-1,2-ethanediamine 

Relevant academic research and scientific papers

Dehydration of Chiral α-Amides to Chiral α-Nitriles Under the Appel Reaction Conditions

An efficient synthesis of Nα-protected amino nitriles from Nα-protected amino acid amides employing Ph3P, I2 and NMM was described. Various amino acid amides, protected by Fmoc, Z and Boc were conveniently conve

Asymmetric Strecker Reactions Catalyzed by Thiourea Phosphonium and Ammonium Salts

The application of asymmetric phase-transfer catalysis to the Strecker reaction of ketimines was realized utilizing bifunctional thiourea-phosphonium salts. The asymmetric Strecker reaction of aldimines was also realized utilizing quaternary ammonium salt

The GAP chemistry for chiral N-phosphonyl imine-based Strecker reaction

Chiral N-phosphonyl imines were found to be efficient electrophiles for reaction with diethylaluminium cyanide, a non-volatile and inexpensive cyanide source. The reaction produced chiral Strecker adducts, α-aminonitriles, in excellent chemical yields (94-98%) and diastereoselectivities (95:5 to >99%). This synthesis was confirmed to follow the GAP chemistry (group-assistant-purification chemistry) process, which can avoid traditional chromatography and recrystallization purifications, i.e., the pure chiral α-aminonitriles bearing a chiral N-phosphonyl group can be simply obtained by washing the solid crude products with hexane. The chiral N-phosphonyl auxiliary can be easily cleaved under mildly acidic conditions and quantitatively recycled by a one-time extraction with n-butanol.

Asymmetric catalytic Strecker reaction of N-phosphonyl imines with Et 2AlCN using amino alcohols and BINOLs as catalysts

The asymmetric catalytic Strecker reaction of achiral N-phosphonyl imines with Et2AlCN has been established. Both free amino alcohols and BINOLs have been proven to be effective catalysts to afford excellent enantioselectivities and yields. The

Isoselenocyanates derived from Boc/Z-amino acids: Synthesis, isolation, characterization, and application to the efficient synthesis of unsymmetrical selenoureas and selenoureidopeptidomimetics

Isoselenocyanates derived from Boc/Z-amino acids are prepared by the reaction of the corresponding isonitriles with selenium powder in presence of triethylamine at reflux. The utility of these new classes of isoselenocyanates in the preparation of selenoureidodipeptidomimetics possessing both amino as well as carboxy termini has been accomplished. The 1H NMR analysis confirmed that the protocol involving the conversion of isonitriles to isoselenocyanates and their use as coupling agents in assembling selenoureido derivatives is free from racemization.

Highly enantioselective titanium-catalyzed cyanation of imines at room temperature

(Figure presented) A highly active and enantioselective titanium-catalyzed cyanatlon of imines at room temperature Is described. The catalyst used Is a partially hydrolyzed titanium alkoxide (PHTA) precatalyst together with a readily available N-salicyl-β-aminoalcohol ligand. Up to 98% ee was obtained with quantitative yields In 15 min of reaction time using 5 mol % of the catalyst. Various N-protecting groups such as benzyl, benzhydryl, Boc, and PMP are tolerated.

Asymmetric catalytic n -phosphonyl imine chemistry: The use of primary free amino acids and Et2AlCN for asymmetric catalytic strecker reaction

(Figure presented) The new asymmetric catalytic Strecker reaction of achiral N-phosphonyl imines has been established. Excellent enantioselectivity (95.2-99.7% ee) and yields (89-97%) have been achieved by using primary free natural amino acids as catalysts and Et2AlCN as nucleophile. This work also presents the novel use of nonvolatile and inexpensive Et 2AlCN in asymmetric catalysis. The N-phosphonyl protecting group enabled simple product purification to be achieved simply by washing the crude products with hexane, which is defined as the GAP chemistry (GAP: Group-Assistant-Purification).(17)It can also be readily cleaved and recycled under mild condition to give a quantitative recovery of N,N′- bis(naphthalen-1-ylmethyl)ethane-1,2-diamine. A new mechanism was proposed for this reaction and was supported by experimental observations.

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

Synthesis of Boc-amino tetrazoles derived from α-amino acids

A simple route for the synthesis of Boc-protected tetrazole analogs of amino acids starting from Nα-Boc amino acids has been described. The [2 + 3] cycloaddition of Boc-α-amino nitrile and sodium azide in the presence of a catalytic amount of zinc bromide yielded the desired tetrazoles in good yields and purity. All the compounds obtained have been characterized by 1H and 13C-NMR and mass spectral studies. Copyright Taylor & Francis Group, LLC.

A convenient new procedure for converting primary amides into nitriles

An operationally simple and high-yielding procedure has been developed for the conversion of primary amides to the corresponding nitriles, using ethyl dichlorophosphate/DBU as the mild dehydrating agent. The Royal Society of Chemistry.