Organocatalytic activity of 4-hydroxy-prolinamide alcohol with different noncovalent coordination sites in asymmetric Michael and direct aldol reactions

Yuko Okuyama, Hiroto Nakano, Yuki Watanabe, Mika Makabe, Mitsuhiro Takeshita, Koji Uwai, Chizuko Kabuto, Eunsang Kwon

Research output: Contribution to journalArticlepeer-review

41 Citations (Scopus)

Abstract

4-Hydroxy-prolinamide alcohol with different noncoordination sites as a molecule showed excellent asymmetric catalytic activity in both the Michael reaction (up to 98% ee) and the direct aldol reaction (up to >99% ee), and the catalyzing reactions with high enantioselectivity are supported by a DFT theoretical study of their transition state.

Original languageEnglish
Pages (from-to)193-197
Number of pages5
JournalTetrahedron Letters
Volume50
Issue number2
DOIs
Publication statusPublished - 2009 Jan 14

Keywords

  • 4-Hydroxy-prolinamide alcohol
  • Aldol reaction
  • DFT calculations
  • Michael reaction
  • Organocatalyst

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Organocatalytic activity of 4-hydroxy-prolinamide alcohol with different noncovalent coordination sites in asymmetric Michael and direct aldol reactions'. Together they form a unique fingerprint.

Cite this