402858-47-3

Upstream product

• 220985-08-0 N-acryloyl-2α-(2-trans-phenylethenyl)-4,4,7α-trimethyl-trans-octahydro-1,3-benzoxazine 
• 402858-23-5 (2S,4aS,7R,8aR)-4,4,7-Trimethyl-2-((E)-styryl)-octahydro-benzo[e][1,3]oxazine 
• 104-55-2 3-phenyl-propenal 
• 55179-51-6 (-)-aminomenthol 
• 402858-38-2 3,13,13-trimethyl-2,3,4,4a,5b,6,11,11a,13,13a-decahydro-1H,5aH-5-oxa-12a-aza-dibenzo[b,h]fluoren-12-one 

Relevant academic research and scientific papers

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.