406937-93-7

Upstream product

• 108-86-1 bromobenzene 
• 124575-31-1 (S)-2-isobutyl-1-tosyl-aziridine 
• 61-90-5 L-leucine 
• 100-59-4 phenylmagnesium chloride 
• 130748-67-3 (2S)-N-(4-methylbenzene)-1-sulfonoamido-4-methylpentan-1-ol 
• 98-59-9 p-toluenesulfonyl chloride 
• 1220-80-0 (S)-4-methyl-2-(toluene-4-sulfonamido)pentanoic acid 

Downstream Products

• 754178-74-0 (S)-4-methyl-1-phenylpentan-2-amine 

Relevant academic research and scientific papers

Development of biisoquinoline-based chiral diaminocarbene ligands: Enantioselective SN2′ allylic alkylation catalyzed by copper-carbene complexes

Chiral biisoquinoline-based diaminocarbene ligands (BIQ) were designed to create a chiral environment extended toward the metal center, which was confirmed by an X-ray structure. The concise ligand synthesis is highlighted by a modified Bischler-Napieralski cyclization of bisamides prepared from readily available chiral phenethylamines, and allows easy variation of the stereodifferentiating groups. The cyclohexyl-BIQ-copper complex is an efficient catalyst for enantioselective SN2′ allylic alkylation with Grignard reagents showing SN2′ regioselectivity higher than 5:1 and enantioselectivity in the range of 68-77% ee.

A new convenient approach to chiral β-aryl(heteroaryl)alkylamines

Chiral β-aryl(heteroaryl)alkylamines have been prepared from N-tosyl alkylaziridines via regiospecific nucleophilic ring opening and subsequent desulfonylation in good to excellent yields. The corresponding aziridines are easily obtained from commercially available (S)-α-amino acids, so this method is the first effective route to asymmetric β-aryl(heteroaryl)alkylamines.