171002-01-0

Upstream product

• 108-98-5 thiophenol 
• 171001-99-3 (2S)-2-[(tert-butoxycarbonyl)amino]-2-phenylethyl 4-methylbenzenesulfonate 
• 110143-62-9 (S)-(+)-<2-<(methylsulfonyl)oxy>-1-phenylethyl>carbamic acid 1,1-dimethylethyl ester 
• 117049-14-6 tert-butyl N-[(1S)-2-hydroxy-1-phenylethyl]carbamate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 882-33-7 diphenyldisulfane 
• 20989-17-7 (2S)-2-phenylglycinol 

Downstream Products

• 209787-98-4 [(S)-2-((S)-Benzenesulfinyl)-1-phenyl-ethyl]-carbamic acid tert-butyl ester 
• 209787-93-9 [(S)-2-((R)-Benzenesulfinyl)-1-phenyl-ethyl]-carbamic acid tert-butyl ester 
• 197020-74-9 (+)-(1R)-1-phenyl-2-(phenylthio)ethylamine 
• 209788-02-3 (S)-2-((R)-Benzenesulfinyl)-1-phenyl-ethylamine 
• 209788-05-6 (S)-2-((S)-Benzenesulfinyl)-1-phenyl-ethylamine 

Relevant academic research and scientific papers

Chiral lithium amido sulfide ligands for asymmetric addition reactions of alkyllithium reagents to aldehydes

Six chiral amino sulfides have been synthesised from the amino acids phenylalanine, phenylglycine and valine. These amino sulfides were used as chiral ligands in the asymmetric addition of n-butyllithium and metyllithium to various aldehydes at low temperatures. The highest stereoselectivities were obtained with benzaldehyde, resulting in 1-phenyl-1-pentanol and 1-phenyl-1-ethanol in enantiomeric excesses of >98.5 and 95%, respectively. These stereoselectivities were significantly higher than those induced by the ether analogues.

Chiral β-amino sulfoxides. Synthesis, configurational assignment and conformational analysis based on X-ray, CD, 1H NMR and theoretical calculations

Enantiomerically pure u and l β-amino sulfoxides have been easily obtained from the respective homochiral α-amino alcohols. The absolute configuration at the created stereogenic centre was assigned by CD spectra and by X-ray analysis. Conformational analysis of the title compounds was carried out using quantum chemical energy-geometry optimization. Thus established conformational behavior explained the strongly configuration dependent NMR spectral patterns observed for the u and l diastereomers.

Synthesis of chiral β-amino sulfides and β-amino thiols from α-amino acids

Bifurcated routes to two series of chiral secondary β-amino sulfides 5a-c and 11a-c have been developed from L-proline and (S)-phenylglycine, respectively. The developed methodology had also led to the synthesis of the tertiary β-amino thiol 7 and the primary β-amino sulfide 12 from L-proline and (S)-phenylglycine, respectively.