Simple primary β-amino alcohol catalyzed enantioselective Diels-Alder reaction of 3-hydroxy-2-pyridones

Toshihisa Takahashi, U. V. Subba Reddy, Yoshihito Kohari, Chigusa Seki, Taniyuki Furuyama, Nagao Kobayashi, Yuko Okuyama, Eunsang Kwon, Koji Uwai, Michio Tokiwa, Mitsuhiro Takeshita, Hiroto Nakano

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)

Abstract

The simple primary β-amino alcohol catalyzed Diels-Alder reaction of 3-hydroxy-2-pyridones as dienes with N-substituted maleimides to provide the highly substituted optically active isoquinuclidines as a single diastereomers in excellent enantioselectivities (up to 98%) with excellent chemical yields (up to 95%) was demonstrated. A range of simple β-amino alcohols were synthesized from the corresponding inexpensive amino acids and their catalytic activity was examined for this reaction.

Original languageEnglish
Pages (from-to)5771-5776
Number of pages6
JournalTetrahedron Letters
Volume57
Issue number51
DOIs
Publication statusPublished - 2016

Keywords

  • 3-Hydroxy-2-pyridone
  • Diels-Alder reaction
  • Enantioselective organocatalysis
  • Primary β-amino alcohol

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Simple primary β-amino alcohol catalyzed enantioselective Diels-Alder reaction of 3-hydroxy-2-pyridones'. Together they form a unique fingerprint.

Cite this