14231-69-7

Upstream product

• 463-71-8 thiophosgene 
• 6273-59-2 2-(benzylamino)-2-phenylethanol 
• 135357-90-3 (2R)-N-benzyl-2-amino-2-phenyl-1-ethanol 
• 100-52-7 benzaldehyde 
• 74879-43-9 (R)-N-benzylidene-2-hydroxy-1-phenylethylamine 
• 14231-57-3 (R)-N-benzyl-2-phenylglycinol 
• 6160-65-2 1,1'-Thiocarbonyldiimidazole 
• 56613-80-0 D-2-phenylglycinol 
• 20989-17-7 (2S)-2-phenylglycinol 

Downstream Products

• 1085994-55-3 (R)-3-benzyl-4-phenylthiazolidin-2-one 
• 1187737-89-8 C₁₇H₁₈INOS 
• 1085994-46-2 S-ethyl N-benzyl-N-(R)-2-iodo-1-phenylethylcarbamathioate 
• 1085994-48-4 S-ethyl N-benzyl-N-1-phenylvinylcarbamothioate 
• 1085994-59-7 (R)-3-benzyl-4-phenylthiazolidin-2-thione 
• 36069-85-9 S-ethyl N-benzylcarbamothioate 
• 98-86-2 acetophenone 
• 100-46-9 benzylamine 
• 1085994-41-7 (R)-S-ethyl-3-benzyl-4-phenyloxazolidin-2-thionium triflate 
• 1085994-44-0 (R)-S-isopropyl-3-benzyl-4-phenyloxazolidin-2-thionium triflate 
• 1085994-38-2 (R)-S-methyl-3-benzyl-4-phenyloxazolidin-2-thionium triflate 

Relevant academic research and scientific papers

Reactivity of (R)-4-phenyloxazolidine-2-thione chiral auxiliary: From deprotection to heterocyclic interconversion

Using (R)-3-benzyl-4-phenyloxazolidin-2-thione (2) as model compound, a sequence of reactions has been established that allows the chiral auxiliary deprotection to furnish a primary amine. Treatment of 2 with ethyl triflate (3b) followed by ring opening with RbI (4b) and HI elimination with DBU, in a one pot process, gave S-ethyl-N-benzyl-N-1-phenylvinylcarbamothioate (5, 95% yield) which acid hydrolysis (9) and saponification liberated benzylamine. Through a mechanistic study, we showed that the activated chiral oxazolidin-2-thione 3b is a tunable intermediate towards the corresponding oxazolidin-2-one 7, thiazolidin-2-one 8 and thiazolidin-2-thione 10. All those reactions were chemoselective and preserved the chiral center. A structural analysis of this series of heterocycles, by NMR and X-ray diffraction, has been performed. The Japan Institute of Heterocyclic Chemistry.