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A highly enantioselective Diels-Alder reaction of 1,2-dihydropyridine using a simple β-amino alcohol organocatalyst for a practical synthetic methodology of oseltamivir intermediate |
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| Authors: | Chonticha SuttibutYoshihito Kohari Ko IgarashiHiroto Nakano Masafumi HiramaChigusa Seki Haruo MatsuyamaNobuhiro Takano Yuko OkuyamaKenichi Osone Mitsuhiro TakeshitaEunsang Kwon |
| Institution: | a Department of Applied Chemistry, Faculty of Engineering, Muroran Institute of Technology, Muroran, Hokkaido 050-8585, Japan b Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan c Research and Analytical Center for Giant Molecules, Graduate School of Sciences, Tohoku University, 6-3 Aoba, Aramaki, Aoba-ku, Sendai 980-8578, Japan |
| Abstract: | An easily prepared chiral amino alcohol catalyst was found to provide an efficient synthetic intermediate of oseltamivir with excellent chemical yield and enantioselectivity (up to 98% yield and up to 98% ee) in enantioselective Diels-Alder reactions of 1,2-dihydropylidines with acroleins. |
| Keywords: | β-Amino alcohol Organocatalyst Diels-Alder reaction 1 2-Dihydropyridine Isoquinuclidine |
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