402858-23-5Relevant academic research and scientific papers
Regio- and diastereoselective tandem addition-carbocyclization promoted by sulfanyl radicals on chiral perhydro-1,3-benzoxazines
Pedrosa, Rafael,Andres, Celia,Duque-Soladana, Juan P.,Maestro, Alicia,Nieto, Javier
, p. 2985 - 2990 (2003)
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
Pedrosa, Rafael,Andres, Celia,Nieto, Javier
, p. 782 - 789 (2007/10/03)
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.
