The Diels-Alder reaction of 1,2-dihydropyridine derivatives (1-phenoxycarbonyl-1,2-dihydropyridine 1 or 1-methoxycarbonyl-1,2-dihydropyridine 4) with N-acryloyl (1S)-2,10-camphorsultam (1S)-2 (or N-acryloyl (1R)-2,10-camphorsultam (1R)-2) in the presence of Lewisacid such as titanium tetrachloride, zirconium tetrachloride, and hafnium tetrachloride afforded the endo-cycloaddition product, 2-azabicyclo[2.2.2]octane derivatives in good yields with excellent diastereoselectivity. The absolute stereochemistry assignment of the endo-cycloaddition product (1S)-5a starting from N-acryloyl (1S)-2,10-camphorsultam (1S)-2hasbeen established to be (1S, 4R, 7S) and the reaction mechanism was proposed.
An efficient synthesis of chiral isoquinuclidines by Diels-Alder reaction using Lewis acid catalyst
Tetrahedron_66(38)p7618-7624.pdf
(775.15KB)
