405144-82-3

Upstream product

• 405144-80-1 (2S,3S,8S,9S,10S)-4-benzyloxycarbonyl-2,3-diphenyl-8-phenylselenenyloctahydrobenzo-1,4-oxazine 
• 405144-79-8 (2S,3S,8S,9S,10S)-2,3-diphenyl-8-phenylselenenyloctahydrobenzo-1,4-oxazine 
• 405144-78-7 (1S,2S)-2-(cyclohex-2'-enylamino)-1,2-diphenylethanol 
• 1521-51-3 rac-3-bromocyclohexene 
• 501-53-1 benzyl chloroformate 
• 530-36-9 (1S,2S)-2-amino-1,2-diphenylethanol 
• 405144-81-2 (2S,3S,9R,10S)-4-benzyloxycarbonyl-2,3-diphenyl-2,3;5,6;9,10-hexahydrobenzo-1,4-oxazine 

Downstream Products

• 405144-83-4 (2S,3S,7R,8R,9S,10S)-4-benzyloxycarbonyl-8-hydroxy-2,3-diphenyl-7-phenylselenenyloctahydrobenzo-1,4-oxazine 
• 405144-84-5 (2S,3S,8S,9S,10S)-4-benzyloxycarbonyl-8-hydroxy-2,3-diphenyl-2,3;5,10;8,9-hexahydrobenzo-1,4-oxazine 

Relevant academic research and scientific papers

Introduction of cis-vicinal amino alcohol functionality into the cyclohexane ring employing (1S,2S)-2-amino-1,2-diphenylethanol: Synthesis of enantiopure aminocyclohexitols

Pd(0)-catalyzed allylic amination of 3-bromocyclohexene with (1S,2S)-2-amino-1,2-diphenylethanol and subsequent intramolecular oxyselenenylation of the resulting allylic amine 6 followed by oxidation-elimination afforded the valuable cis-fused bicyclic olefin 10. Oxyselenenylation of cyclohexene with (1S,2S)-N-(benzyloxycarbonyl)-2-amino-1,2-diphenylethanol and subsequent oxidation-elimination gave the allylic ether 18. Intramolecular aminoselenenylation of 18 followed by oxidation-elimination provided the cis-fused bicyclic olefin 21, which is the regioisomer of 10. Further stereoselective transformation of 10 afforded enantiopure aminocyclohexitols.