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An efficient synthetic methodology of chiral isoquinuclidines by the enantioselective Diels-Alder reaction of 1,2-dihydropyridines using chiral cationic palladium-phosphinooxazolidine catalyst |
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| Authors: | Hiroto Nakano Natsumi Tsugawa Kouichi Takahashi Yuko Okuyama Reiko Fujita |
| Affiliation: | Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan |
| 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. |
| Keywords: | Enantioselective Diels-Alder reaction 1,2-Dihydropyridine Chiral cationic palladium-phosphinooxazolidine catalyst Chiral isoquinuclidines Chiral piperidines |
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