863016-86-8

Upstream product

• 6651-36-1 1-(Trimethylsilyloxy)cyclohexene 
• 127-65-1 chloroamine-T 
• 98-59-9 p-toluenesulfonyl chloride 
• 931-15-7 (1R,2R)-2-aminocyclohexanol 

Downstream Products

• 882409-32-7 (1R,2S)-cis-(N-2-benzylamino-cyclohexyl)-toluenesulfonamide 
• 58825-94-8 (1R,2S)-cis-(N-2-amino-cyclohexyl)-toluenesulfonamide 
• 882409-31-6 (2S,7aR)-2-phenyl-1-(toluene-4-sulfonyl)-2,4,5,6,7,7a-hexahydro-1H-benzoimidazole 

Relevant academic research and scientific papers

Resolution of racemic 2-aminocyclohexanol derivatives and their application as ligands in asymmetric catalysis

A preparatively easy and efficient protocol for the resolution of racemic 2-aminocyclohexanol derivatives is described, delivering both enantiomers with >99% enantiomeric excess (ee) by sequential use of (R)- and (S)-mandelic acid. A simple aqueous workup procedure permits the isolation of the amino alcohols in analytically pure form and the almost quantitative recovery of mandelic acid. Debenzylation of enantiopure trans-2-(N-benzyl)amino-1- cyclohexanol by hydrogenation and subsequent derivatization give access to a broad variety of diversely substituted derivatives. Furthermore, the corresponding cis isomers are readily available. Applications of these optically active aminocyclohexanols in catalyzed asymmetric phenyl transfer reactions to benzaldehydes and transfer hydrogenations of aryl ketones lead to products with up to 96% ee.

OsO4-catalyzed amination of silyl enol ethers: Enantioselective synthesis of α-amino ketones

Osmium tetroxide catalyzed asymmetric aminohydroxylation of silyl enol ethers using cinchona alkaloids as chiral ligands and chloramine-T as the nitrogen source affords enantiomerically pure α-amino ketones.