203190-41-4

Upstream product

• 7689-50-1 N-benzyl glycine hydrochloride 
• 454251-75-3 (2S,4aS,7R,8aR)-N-allyl-2-formyl-4,4,7-trimethyl-octahydro-1,3-benzoxazine 
• 115156-56-4 (1R,2S,5R)-5-methyl-2-<1-methyl-1-(benzylamino)ethyl>cyclohexan-1-ol 
• 454251-71-9 (2S,4aS,7R,8aR)-N-allyl-2-hydroxymethyl-4,4,7-trimethyl-octahydro-1,3-benzoxazine 
• 454251-70-8 (2S,4aS,7R,8aR)-2-hydroxymethyl-4,4,7-trimethyl-octahydro-1,3-benzoxazine 
• 55179-51-6 (-)-aminomenthol 
• 106-95-6 allyl bromide 

Downstream Products

• 203190-42-5 (2S,3S,4aS,7R,8aR)-3-Allyl-2-(2-bromo-phenyl)-4,4,7-trimethyl-octahydro-benzo[e][1,3]oxazine 
• 186597-31-9 (3'S)-8-(3'-methylpyrrolidinyl)menthol 
• 186597-30-8 (3'R)-8-(3'-methylpyrrolidinyl)menthol 
• 188644-86-2 N-(8-mentholyl)-(3aR,6R,7aR)-3a,6-epoxy-3a,6,7,7a-tetrahydroisoindoline 
• 188644-85-1 N-(8-mentholyl)-(3aS,6S,7aS)-3a,6-epoxy-3a,6,7,7a-tetrahydroisoindoline 
• 1666-13-3 diphenyl diselenide 
• 235093-81-9 N-allyl-2α-(phenylseleno)methyl-4,4,7α-trimethyl-trans-octahydro-1,3-benzoxazine 

Relevant academic research and scientific papers

A novel synthesis of enantiopure octahydropyrrolo[3,4-b]pyrroles by intramolecular [3 + 2] dipolar cycloaddition on chiral perhydro-1,3-benzoxazines

(Matrix presented) Condensation of N-substituted glycines with chiral 3-allyl-2-formyl perhydro-1,3-benzoxazines forms an azomethine ylide that cyclizes to give octahydropyrrolo[3,4-b]pyrrole derivatives. The [3 + 2] dipolar cycloadditions are stereoespec

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.

Unexpected stereoselective 6-exo versus 7-endo aryl radical cyclisation controlled by positional isomers in a chiral octahydro-1,3-benzoxazine moiety

Chiral perhydro-1,3-benzoxazines which carry both olefinic and bromo-aromatic substituents undergo stereo- and regio- radical cyclisations mediated by Bu3SnH. Diastereomeric six-membered and seven-membered rings are formed in positional isomers through selective 6-exo and 7-endo attack respectively.