Enantioselective Diels-Alder reaction of 1,2-dihydropyridines with aldehydes using β-amino alcohol organocatalyst

Yoshihito Kohari, Yuko Okuyama, Eunsang Kwon, Taniyuki Furuyama, Nagao Kobayashi, Teppei Otuki, Jun Kumagai, Chigusa Seki, Koji Uwai, Gang Dai, Tatsuo Iwasa, Hiroto Nakano

研究成果: Article査読

30 被引用数 (Scopus)

抄録

(Chemical Equation Presented) The enantioselective Diels-Alder reaction of 1,2-dihydropyridines with aldehydes using an easily prepared optically active β-amino alcohol catalyst was found to provide optically active isoquinuclidines, an efficient synthetic intermediate of pharmaceutically important compounds such as oseltamivir phosphate, with a satisfactory chemical yield and enantioselectivity (up to 96%, up to 98% ee). In addition, the obtained highly optically pure isoquinuclidine was easily converted to an optically active piperidine having four successive carbon centers.

本文言語English
ページ(範囲)9500-9511
ページ数12
ジャーナルJournal of Organic Chemistry
79
20
DOI
出版ステータスPublished - 2014 10 17

ASJC Scopus subject areas

  • Organic Chemistry

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