220985-08-0

Upstream product

• 814-68-6 acryloyl chloride 
• 402858-23-5 (2S,4aS,7R,8aR)-4,4,7-Trimethyl-2-((E)-styryl)-octahydro-benzo[e][1,3]oxazine 
• 14371-10-9 (E)-3-phenylpropenal 
• 104-55-2 3-phenyl-propenal 
• 55179-51-6 (-)-aminomenthol 

Downstream Products

• 402858-53-1 (3aS,9aS)-N-(8-mentholyl)-3a,4,9,9a-tetrahydrobenz[f]isoindoline 
• 402858-47-3 (3aR,9aR)-N-(8-mentholyl)-3a,4,9,9a-tetrahydrobenz[f]isoindoline 
• 565177-26-6 (1R,5S,6R)-N-(menthol-8-yl)-6-phenyl-3-azabicyclo[3.2.0]heptane 
• 565177-31-3 (1S,5R,6S)-N-(menthol-8-yl)-6-phenyl-3-azabicyclo[3.2.0]heptane 
• 883146-14-3 (1R,5S,6R)-6-phenyl-3-aza-bicyclo[3.2.0]heptane 
• 565177-10-8 (2S,2aR,2bS,3aR,5R,7aS,10aS)-2-phenyl-5,8,8-trimethylperhydrocyclobuta[3,4]pyrrolo[2,1-b]-[1,3]benzoxazin-10-one 
• 565177-09-5 (2R,2aS,2bS,3aR,5R,7aS,10aR)-2-phenyl-5,8,8-trimethylperhydrocyclobuta[3,4]pyrrolo[2,1-b]-[1,3]benzoxazin-10-one 
• 402858-36-0 N-acryloyl-2β-(2-trans-phenylethenyl)-4,4,7α-trimethyl-trans-octahydro-1,3-benzoxazine 

Relevant academic research and scientific papers

Regio- and diastereoselective tandem addition-carbocyclization promoted by sulfanyl radicals on chiral perhydro-1,3-benzoxazines

Radical addition-carbocyclization of 2-allyl-3-acyloyl-substituted perhydro-1,3-benzoxazines readily provides 3,4-disubstituted pyrrolidinone derivatives with total regioselectivity and good diastereoselectivity. The key step of the reaction is a tandem addition-5-exo-cyclization promoted by a sulfanyl radical.

Stereocontrolled IMDA reaction of styrene derivatives. A way to enantiopure 3a,4,9,9a-tetrahydrobenz[f]isoindolines

IMDA reactions on chiral perhydro-1,3-benzoxazines, derived from (-)-8-amino menthol, bearing a styrene substituent at C-2 acting as diene and an acryl amide acting as dienophile occur with high stereoselection and excellent chemical yields. After elimination of the chiral appendage, enantiopure 3a,4,9,9a-tetrahydrobenz[f]isoindolines are prepared in this way. The effect of the substituents at both diene and dienophile are studied, showing that a methyl group at C-1 in the diene inhibited the reaction, while the ene adduct, instead of the IMDA product, was obtained when a methyl group was at C-2.