1219152-49-4

Upstream product

• 81167-39-7 methyl N-(diphenylmethylene)glycinate 
• 150884-50-7 benzaldehyde N-boc imine 
• 155396-71-7 tert-butyl N-(phenyl(phenylsulfonyl)methyl)carbamate 

Downstream Products

• 1373550-33-4 methyl (2S,3R)-2-amino-3-((tert-butoxycarbonyl)amino)-3-phenylpropanoate 
• 1448851-90-8 (2S,3R)-methyl 5,6-dioxo-3-phenylpiperazine-2-carboxylate 
• 1373550-29-8 benzyl (3S,4R)-2-oxo-4-phenylazetidin-3-ylcarbamate: 
• 1448851-91-9 (4R,5S)-methyl 2-(4-bromophenyl)-4-phenyl-4,5-dihydro-1Himidazole-5-carboxylate 
• 1448851-92-0 (5S,8S,9R,12S)-methyl 12-benzyl-5,16,16-trimethyl-3,6,11,14-tetraoxo-1,9-diphenyl-2,15-dioxa-4,7,10,13-tetraazaheptadecane-8-carboxylate 
• 1373550-28-7 (2S,3R)-methyl 3-amino-2-(benzyloxycarbonylamino)-3-phenylpropanoate 
• 675124-80-8 methyl [(2S,3R)-2,3-diamino-3-phenyl]propanoate 

Relevant academic research and scientific papers

Cyclopropenimine-catalyzed enantioselective mannich reactions of tert -butyl glycinates with N -Boc-imines

Cyclopropenimine 1 is shown to catalyze Mannich reactions between glycine imines and N-Boc-aldimines with high levels of enantio- and diastereocontrol. The reactivity of 1 is shown to be substantially greater than that of a widely used thiourea cinchona alkaloid-derived catalyst. A variety of aryl and aliphatic N-Boc-aldimines are effective substrates for this transformation. A preparative-scale reaction to deliver >90 mmol of product is shown using 1 mol % catalyst. The products of this transformation can be converted into several useful derivatives.

CYCLOPROPENIMINE CATALYST COMPOSITIONS AND PROCESSES

The present invention provides, inter alia, a cyclopropenimine Br?nsted base catalyst and a cyclopropenimine scaffold for use as a Br?nsted base catalyst. This cyclopropenimine has the structure (100). Methods for making such a cyclopropenimine are also provided. Further provided are processes for carrying out an organic synthetic reaction and processes for catalyzing a proton transfer reaction enantioselectively using such a cyclopropenimine Br?nsted base catalyst.

Substrate-controlled diastereoselectivity switch in catalytic asymmetric direct mannich reaction of glycine derivatives with imines: from anti- to syn-α,β-diamino acids

(Chemical equation Presented) Back and forth: A diastereoselectivity switch has been devised in the Fesulphos-CuI-catalyzed glycine direct Mannich reaction with N-(8-quinolyl)sulfonyl imines by tuning the steric and electronic properties of the glycine component (see scheme). αβ-Diamino acids of syn configuration are produced under high diastereo- and enantiocontrol with glycinate esters derived from electron-deficient benzophenonetype ketimines, in contrast to aldiminederived pronucleophiles that lead to anti-configured products.

Highly enantio- And diastereoselective mannich reactions of glycine schiff bases with in situ generated N-boc-imines catalyzed by a cinchona alkaloid thiourea

(Figure Presented) Highly ena(Figure Presented)ntlo- and dlastereoselectlve organocatalytlc Mannlch reactions of glycine Schiff bases with N-Boc-protected lmlnes are described. Imlnes were generated In situ from bench-stable a-amldo sulfones. Catalysis mediated by a cinchona alkaloid thiourea provided optically active α,βdlamlno acid derivatives with up to 99% ee and near-perfect dlastereoselection.