1373550-33-4

Upstream product

• 81167-39-7 methyl N-(diphenylmethylene)glycinate 
• 150884-50-7 benzaldehyde N-boc imine 
• 1219152-49-4 methyl (2S,3R)-3-(tert-butoxycarbonylamino)-2-(diphenylmethyleneamino)-3-phenylpropanoate 
• 1572214-77-7 tert-butyl (R)-[(2S,5R)-5-isopropyl-3,6-dimethoxy-2,5-dihydropyrazin-2-yl](phenyl)methylcarbamate 
• 177896-09-2 tert-butyl benzylidenecarbamate 
• 1373550-32-3 methyl (2S,3R)-2-(((benzyloxy)carbonyl)amino)-3-((tert-butoxycarbonyl)amino)-3-phenylpropanoate 

Downstream Products

• 675124-80-8 methyl [(2S,3R)-2,3-diamino-3-phenyl]propanoate 
• 1448851-90-8 (2S,3R)-methyl 5,6-dioxo-3-phenylpiperazine-2-carboxylate 
• 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 
• 1373550-29-8 benzyl (3S,4R)-2-oxo-4-phenylazetidin-3-ylcarbamate: 
• 1373550-28-7 (2S,3R)-methyl 3-amino-2-(benzyloxycarbonylamino)-3-phenylpropanoate 

Relevant academic research and scientific papers

Asymmetric synthesis of syn and anti methyl 2,3-diamino-3-phenylpropanoate derivatives from N-substituted imines and Sch?llkopf's bislactim ether

Abstract The reaction between differently N-substituted benzaldimines and (2R)-Sch?llkopf's bislactim ether was studied: the azaenolate addition to imines followed by hydrolysis of the resulting adducts gave syn-(2S,3R) and anti-(2S,3S)-methyl 2,3-diamino-3-phenylpropanoate derivatives in good yields. The configurations of the newly formed stereocenters of α,β-diamino acids were assigned on the basis of the 1H NMR analysis and by comparison with known products. The diastereoisomeric ratios were explained taking into account the effect of the substituent present on the imine nitrogen on the transition state stability. This method represents a new approach for stereoselective synthesis of α,β-diamino acids.

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.

Stereocontrolled synthesis of vicinal diamines by organocatalytic asymmetric mannich reaction of N -protected aminoacetaldehydes: Formal synthesis of (-)-agelastatin A

The 1,2-diamine (vicinal diamine) motif is present in a number of natural products with interesting biological activity and in many chiral molecular catalysts. The efficient and stereocontrolled synthesis of enantioenriched vicinal diamines is still a challenge to modern chemical methodology. We report here both syn- and anti-selective asymmetric direct Mannich reactions of N-protected aminoacetaldehydes with N-Boc-protected imines catalyzed by proline and the axially chiral amino sulfonamide (S)-3. This organocatalytic process represents the first example of a Mannich reaction using Z- or Boc-protected aminoacetaldehyde as a new entry of α-nitrogen functionalized aldehyde nucleophile in enamine catalysis. The obtained optically active vicinal diamines are useful chiral synthons as exemplified by the formal synthesis of (-)-agelastatin A.