A comparative study of the multicomponent Ugi reactions of an oxabicycloheptene-based β-amino acid in water and in methanol

Iván Kanizsai, Z. Szakonyi, Reijo Sillanpää, F. Fülöp

Research output: Contribution to journalArticle

31 Citations (Scopus)

Abstract

Di-exo-3-amino-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic acid 1, five aldehydes and two isocyanides were reacted both in methanol and in water to prepare a 10-membered β-lactam library via a Ugi-4-centre-3-component reaction. The yields were found to be similar in water and methanol. The diastereoselectivities of the aqueous reactions were similar, though in a few cases higher than those in methanol. The benefits of water are the facile isolation of the precipitated product and the shorter reaction time.

Original languageEnglish
Pages (from-to)9113-9116
Number of pages4
JournalTetrahedron Letters
Volume47
Issue number51
DOIs
Publication statusPublished - Dec 18 2006

Fingerprint

Methanol
Amino Acids
Water
Lactams
Cyanides
Carboxylic Acids
Aldehydes
2-amino-7-oxabicyclo(2.2.1)hept-5-ene

Keywords

  • Bicyclic β-amino acid
  • Intramolecular Ugi reaction
  • Multicomponent reaction

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

A comparative study of the multicomponent Ugi reactions of an oxabicycloheptene-based β-amino acid in water and in methanol. / Kanizsai, Iván; Szakonyi, Z.; Sillanpää, Reijo; Fülöp, F.

In: Tetrahedron Letters, Vol. 47, No. 51, 18.12.2006, p. 9113-9116.

Research output: Contribution to journalArticle

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