An efficient synthesis of chiral isoquinuclidines by Diels–Alder reaction using Lewis acid catalyst

…, C Seki, H Nakano, M Takeshita, N Oshikiri, M Iyoda…

Index: Hirama, Masafumi; Kato, Yuji; Seki, Chigusa; Nakano, Hiroto; Takeshita, Mitsuhiro; Oshikiri, Noriko; Iyoda, Masahiko; Matsuyama, Haruo Tetrahedron, 2010 , vol. 66, # 38 p. 7618 - 7624

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Citation Number: 11

Abstract

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 Lewis acid, such as titanium tetrachloride, zirconium tetrachloride, and hafnium tetrachloride afforded the endo-cycloaddition product, 2-azabicyclo [2.2. 2] octane derivatives in good ...