235093-69-3

Upstream product

• 107-86-8 3,3-dimethyl acrylaldehyde 
• 235093-65-9 N-(phenylseleno)ethyl-8-aminomenthol 
• 1666-13-3 diphenyl diselenide 
• 71338-48-2 phenylselanylacetaldehyde 
• 55179-51-6 (-)-aminomenthol 
• 115156-56-4 (1R,2S,5R)-5-methyl-2-<1-methyl-1-(benzylamino)ethyl>cyclohexan-1-ol 
• 235093-64-8 2-(phenylseleno)methylperhydro-1,3-benzoxazine 

Downstream Products

• 323999-97-9 (1R,2S,5R)-2-{1-[((S)-1,3-Dimethyl-but-2-enyl)-(2-phenylselanyl-ethyl)-amino]-1-methyl-ethyl}-5-methyl-cyclohexanol 
• 323999-94-6 8-amino-O-tert-butyldimethylsilyl-N-phenylselenoethyl-N-prenylmenthol 
• 323999-98-0 8-[(2'S,3'S)-3'-isopropyl-2'-methylpyrrolidinyl] menthol 
• 235093-95-5 (3'S)-8-(3'-isopropylpyrrolidinyl)menthol 
• 89-82-7 pulegone 
• 323999-92-4 8-amino-N-phenylselenoethyl-N-prenylmenthol 

Relevant academic research and scientific papers

Regio- and stereoselective 5-exo radical cyclizations on a chiral perhydro-1,3-benzoxazine moiety. An access to enantiopure 3-alkylpyrrolidines

Both enantiomers of chiral, nonracemic 3-alkyl-substituted pyrolidines are prepared by diastereo-selective 5-exo-trig cyclization on (-)-8- aminomenthol-derived perhydro-1,3-benzoxazines used as chiral auxiliaries, followed by elimination of the menthol appendage. The diastereoselective radical cyclization is promoted by tributyltin hydride and occurs on a 3- aza-5-hexenyl-type radical, leading to five-membered rings in high yield. The stereocontrol of the cyclization is strongly influenced by 1,3-allylic strain so that an appropriate substitution pattern on the olefin-acceptor and the presence of a vicinal stereocenter are crucial for achieving good diastereoselectivity. The enantiopure pyrrolidines are obtained in three steps with concomitant recovering of the starting (+)-pulegone auxiliary.