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

Research output: Contribution to journalArticlepeer-review

29 Citations (Scopus)

Abstract

(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.

Original languageEnglish
Pages (from-to)9500-9511
Number of pages12
JournalJournal of Organic Chemistry
Volume79
Issue number20
DOIs
Publication statusPublished - 2014 Oct 17

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint Dive into the research topics of 'Enantioselective Diels-Alder reaction of 1,2-dihydropyridines with aldehydes using β-amino alcohol organocatalyst'. Together they form a unique fingerprint.

Cite this