872874-36-7

Upstream product

• 35203-91-9 8-quinolinesulfonamide 
• 100-52-7 benzaldehyde 

Downstream Products

• 1087163-25-4 (2S,3S)-methyl 2-(benzylamino)-3-phenyl-3-[(8-quinolyl)sulfonylamino]propanoate 
• 1087163-48-1 (2S,3S) methyl 2-(benzylamino)-2-methyl-3-phenyl-3-[(8-quinolyl)sulfonylamino]propanoate 
• 1219152-67-6 C₃₅H₃₁N₃O₄S 
• 1219152-74-5 (2S,3R)-methyl 2-[(bis(4-fluorophenyl)methylene)amino]-3-phenyl-3-[(8-quinolyl)sulfonylamino]propanoate 
• 1219152-65-4 (2S,3R)-tert-butyl 2-[(diphenylmethylene)amino]-3-phenyl-3-[(8-quinolyl)sulfonylamino]propanoate 
• 1219152-60-9 (2S,3R)-methyl 2-[(diphenylmethylene)amino]-3-phenyl-3-[(8-quinolyl)sulfonylamino]propanoate 
• 1219152-73-4 (2S,3R)-methyl 2-[(bis(4-chlorophenyl)methylene)amino]-3-phenyl-3-[(8-quinolyl)sulfonylamino]propanoate 
• 1219152-70-1 (2S,3R)-tert-butyl 2-[(bis(4-chlorophenyl)methylene)amino]-3-phenyl-3-[(8-quinolyl)sulfonylamino]propanoate 
• 1219152-72-3 (2S,3R)-tert-butyl 2-[(bis(4-fluorophenyl)methylene)amino]-3-phenyl-3-[(8-quinolyl)sulfonylamino]propanoate 

Relevant academic research and scientific papers

First example of an organocatalytic asymmetric Mannich reaction between aldimines of glycinates and sulphonyl imines

The catalytic enantioselective Mannich-type reaction between glycinate Schiff base and imines has been one of the most efficient routes for accessing α,β-diamino acids. However, the glycinate Schiff bases used in the references were almost ketimines. Only

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.

Direct Mannich reaction of glycinate Schiff bases with N-(8-quinolyl) sulfonyl imines: A catalytic asymmetric approach to anti-α,β-diamino esters

An efficient catalytic enantioselective direct Mannich reaction of glycinate Schiff bases with aryl imines leading to anticonfigured orthogonally protected α,β-diaminoesters has been realized. Keys to success in this new catalyst system are the use of Fesulphos/Cu(CH3CN)4PF6 (3-5 mol%) as a Lewis acid catalyst and readily available N-(8-quinolyl)sulfonyl-protected aldimines as substrates, affording excellent levels of diastereo- (typically anti/syn >90:10) and enantiocontrol (typically ≥90% ee). A remarkable feature of this catalyst system is that it allows the construction of products with a tetrasubstituted carbon stereocenter at C-α in a highly diastereo- and enantiocontrolled manner. Copyright