Studies on the synthesis of DMAP derivatives by diastereoselective Ugi reactions

Hiroki Mandai, Shunsuke Irie, Koichi Mitsudo, Seiji Suga

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

Diastereoselective Ugi reactions of DMAP-based aldehydes with α-amino acids and tert-butyl isocyanide were examined. The reactions of 4-(dimethylamino)-2-pyridinecarboxaldehyde with various α-amino acids afforded 2-substituted DMAP derivatives with low diastereoselectivity. On the contrary, reactions with 4-(dimethylamino)-3-pyridinecarboxaldehyde delivered 3-substituted DMAP derivatives with moderate to high diastereoselectivity. The combination of α-amino acid and DMAP-based aldehyde is thus important to achieve high diastereoselectivity. Kinetic resolution of a secondary alcohol using a chiral DMAP derivative obtained through these reactions was also examined.

Original languageEnglish
Pages (from-to)8815-8832
Number of pages18
JournalMolecules
Volume16
Issue number10
DOIs
Publication statusPublished - Oct 1 2011

Keywords

  • Chiral DMAP
  • Kinetic resolution
  • Multicomponent reaction
  • Ugi reaction

ASJC Scopus subject areas

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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