675124-80-8

Upstream product

• 1373550-32-3 methyl (2S,3R)-2-(((benzyloxy)carbonyl)amino)-3-((tert-butoxycarbonyl)amino)-3-phenylpropanoate 
• 1373550-33-4 methyl (2S,3R)-2-amino-3-((tert-butoxycarbonyl)amino)-3-phenylpropanoate 
• 150884-50-7 benzaldehyde N-boc imine 
• 1219152-49-4 methyl (2S,3R)-3-(tert-butoxycarbonylamino)-2-(diphenylmethyleneamino)-3-phenylpropanoate 
• 1403165-41-2 (2S,3R)-methyl 2-amino-3-(4-nitrophenylsulfonamido)-3-phenylpropanoate 
• 63160-16-7 4-nitro-N-(phenylmethylene)benzenesulfonamide 
• 251113-73-2 (-)-methyl [(2S,4S,5R,S_S)-2,5-diphenyl-1-(p-tolylsulfinyl)-1,3-imidazolidin-4-yl]carboxylate 
• 177896-09-2 tert-butyl benzylidenecarbamate 

Downstream Products

• 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 

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.

Syn-selective asymmetric mannich reaction of sulfonyl imines with iminoesters catalyzed by the N,N,N-tridentate bis(imidazolidine)pyridine (PyBidine)-Cu(OTf)2 complex

Chiral ligand: The [PyBidine-Cu(OTf)2] (Tf= trifluoromethanesulfonate) complex catalyzed the asymmetric Mannich reaction of sulfonyl imines and iminoesters to give the products in a high syn-selective manner. For both 4-toluene (Ts)- and 4-nitrophenylsulfonyl (Ns)-imines, the syn-adducts were obtained in up to 99 % ee (see scheme). Copyright

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.

Enantio- and diastereoselective catalytic mannich-type reaction of a glycine schiff base using a chiral two-center phase-transfer catalyst

(Chemical Equation Presented) Optically active α,β-diamino acids are prepared under asymmetric phase-transfer reaction conditions from a glycine Schiff base and N-protected imines with a tartrate-derived diammonium salt (TaDiAS) as the phase-transfer cata

Fine-Tuned Aminal Cleavage: A Concise Route to Differentially Protected Enantiopure syn-α,β-Diamino Esters

A survey of routes for aminal cleavage of N-sulfinylimidazolidines has been carried out, and selective conditions to cleave the aminal moiety while preserving the sulfinamide group unaltered have been found. Thus, the treatment of enantiopure N-sulfinylimidazolidines with aqueous H3PO 4 in THF affords enantiopure N-sulfinyldiamino esters in excellent yields, while the presence of MeOH as cosolvent allows for the simultaneous removal of the sulfinamide group and aminal cleavage. The behavior of these substrates in a variety of chemical transformations has been explored.