156022-72-9

Upstream product

• 4530-20-5 BOC-glycine 
• 56613-80-0 D-2-phenylglycinol 
• 66866-43-1 N-(t-butoxycarbonyl)glycyl i-butyl carbonate 

Downstream Products

• 180285-19-2 (2S,6R)-6-Benzyl-4-((R)-2-methoxy-1-phenyl-ethyl)-piperazine-1,2-dicarboxylic acid 1-tert-butyl ester 
• 180285-15-8 (R)-2-Benzyl-4-((R)-2-methoxy-1-phenyl-ethyl)-piperazine-1-carboxylic acid tert-butyl ester 
• 180285-18-1 (2S,6R)-4-((R)-2-Methoxy-1-phenyl-ethyl)-6-methyl-piperazine-1,2-dicarboxylic acid 1-tert-butyl ester 
• 180285-13-6 (R)-2-Benzyl-4-((R)-2-hydroxy-1-phenyl-ethyl)-piperazine-1-carboxylic acid tert-butyl ester 
• 180285-14-7 (R)-4-((R)-2-Methoxy-1-phenyl-ethyl)-2-methyl-piperazine-1-carboxylic acid tert-butyl ester 
• 180285-24-9 (2S,6R)-6-Benzyl-piperazine-1,2-dicarboxylic acid 1-tert-butyl ester 
• 156022-79-6 (R)-2-Benzyl-4-((R)-2-hydroxy-1-phenyl-ethyl)-3-oxo-piperazine-1-carboxylic acid tert-butyl ester 
• 156022-76-3 (R)-4-((R)-2-Hydroxy-1-phenyl-ethyl)-2-methyl-3-oxo-piperazine-1-carboxylic acid tert-butyl ester 
• 156022-74-1 1,1-dimethylethyl (R)-2,5-diaza-5-(bromoacetyl)-9,9,10,10-tetramethyl-8-oxa-6-phenyl-9-silaundecanoate 
• 180285-10-3 (R)-1-<1,1-(dimethylethoxycarbonyl)>-4-(4,4,5,5-tetramethyl-1-phenyl-3-oxa-4-sila-hexyl)piperazin-3-one 
• 156022-73-0 1,1-dimethylethyl (R)-2,5-diaza-9,9,10,10-tetramethyl-8-oxa-6-phenyl-9-silaundecanoate 
• 156022-75-2 (R)-1-<1,1-(dimethylethoxycarbonyl)>-4-(2-hydroxy-1-phenylethyl)piperazin-3-one 
• 180285-12-5 (R)-4-((R)-2-Hydroxy-1-phenyl-ethyl)-2-methyl-piperazine-1-carboxylic acid tert-butyl ester 
• 180285-08-9 1,1-dimethylethyl (R)-2,5-diaza-7-hydroxy-6-phenylheptanoate 

Relevant academic research and scientific papers

Employing the structural diversity of nature: Development of modular dipeptide-analogue ligands for ruthenium-catalyzed enantioselective transfer hydrogenation of ketones

A library of novel dipeptideanalogue ligands based on the combination of tert-butoxycarbonyl(N-Boc)-protected a-amino acids and chiral vicinal amino alcohols were prepared. These highly modular ligands were combined with [{RuCl2(p-cymene)}2 and the resulting metal complexes were screened as catalysts for the enantioselective reduction of acetophenone under transfer hydrogenation conditions using 2-propanol as the hydrogen donor. Excellent enantioselectivity of 1-phenylethanol (up to 98% ee) was achieved with several of the novel catalysts. Although most of the ligands contained two stereocenters, it was demonstrated that the absolute configuration of the product alcohol was determined by the configuration of the amino acid part of the ligand. Employing ligands based on L-amino acids generated S-configured products, and catalysts based on Damino acids favored the formation of the R-configured alcohol. The combination N-Boc-L-alanine and (R)-phenylglycinol (Boc-L-Ab) or its enantiomer (N-Boc-D-alanine and (S)-phenylglycinol, Boc-D-Aa) proved to be the best ligands for the reduction process. Transfer hydrogenation of a number of aryl alkyl ketones were evaluated and excellent enantioselectivity, up to 96 % ee, was obtained.

Asymmetric synthesis; XXXVII: Synthesis of 2,6-disubstituted piperazines from chiral non-racemic lactams

General and convenient syntheses of optically active 2,6-disubstituted piperazines are described. The method is based on diastereoselective alkylation of lactam 8 derived from (R)-(-)-phenylglycinol followed by a regio- and diastereoselective functionalisation of carbamates 10c and 10d. This procedure allowed the preparation of new α-amino acids 15 and 16.

Asymmetric synthesis. XXXI. Synthesis of 2-substituted piperazines from chiral non-racemic lactams

The preparation of lactam 2 from R-(-)-phenylglycinol and N-Boc glycine is described. Diastereoselective alkylation of 2 allowed the preparation of piperazine derivatives in an optically pure form.