36069-85-9

Upstream product

• 55365-86-1 benzylthiocarbamic acid O-ethyl ester 
• 75-03-6 ethyl iodide 
• 100-46-9 benzylamine 
• 2941-64-2 Ethyl chlorothioformate 
• 1085994-41-7 (R)-S-ethyl-3-benzyl-4-phenyloxazolidin-2-thionium triflate 
• 1085994-48-4 S-ethyl N-benzyl-N-1-phenylvinylcarbamothioate 
• 14231-69-7 (R)-3-benzyl-4-phenyloxazolidine-2-thione 
• 14231-57-3 (R)-N-benzyl-2-phenylglycinol 
• 74879-43-9 (R)-N-benzylidene-2-hydroxy-1-phenylethylamine 
• 100-52-7 benzaldehyde 
• 7647-01-0 hydrogenchloride 
• 71-43-2 benzene 

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.