Tetrahedron

An efficient synthetic methodology of chiral isoquinuclidines by the enantioselective Diels–Alder reaction of 1, 2-dihydropyridines using chiral cationic palladium– …

H Nakano, N Tsugawa, K Takahashi, Y Okuyama…

Index: Nakano, Hiroto; Tsugawa, Natsumi; Takahashi, Kouichi; Okuyama, Yuko; Fujita, Reiko Tetrahedron, 2006 , vol. 62, # 47 p. 10879 - 10887

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Citation Number: 29

Abstract

High purity chiral isoquinuclidines (97% ee) were obtained from the enantioselective Diels– Alder reaction of 1-phenoxycarbonyl-1, 2-dihydropyridine with 1-benzyl-2- acryloylpyrazolidin-3-one using chiral cationic palladium–phosphinooxazolidine (Pd–POZ) catalyst. The obtained DA adduct was easily converted to the chiral piperidine derivative bearing three stereogenetic centers in the structure.