| Abstract
| - Diastereoselective intramolecular Diels−Alder reaction on 3-allyl-2-furyl- or 3-furfuryl-2-vinyl-substituted chiral perhydro-1,3-benzoxazines derived from (−)-aminomenthol is described. The [4+ 2] cycloaddition is highly stereo- and regioselective leading to the thermodynamic adducts asmajor products. Reduction of the N,O-acetal, followed by elimination of the menthol appendage,allows both enantiomers of disubstituted epoxy tetrahydroisoindolines to be prepared. Nucleophilicring opening of the N,O-moiety in the adducts by magnesium or aluminum derivatives, followedby elimination of the menthol, leads to the synthesis of enantiopure regioisomeric trisubstitutedepoxy tetrahydroisoindolines with up to five stereocenters.
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