Solid-phase synthesis: Intramolecular azomethine ylide cycloaddition (→proline) and carbanilide cyclization (→hydantoin) reactions

Young Dae Gong, Samir Najdi, Marilyn M. Olmstead, Mark J. Kurth

Research output: Contribution to journalArticle

72 Scopus citations

Abstract

An efficient, diastereoselective route to 2,5,6,7-tetrasubstituted-1H- pyrrolo[1,2-c]imidazoles has been developed using solid-phase intramolecular azomethine ylide cycloaddition and carbanilide cyclization chemistries. To successfully execute this eight-step protocol in the solid phase, it was necessary to insert a spacer moiety between the resin and glycinate functional group. Experiments addressing the stereoselectivity of the 1,3- dipolar cycloaddition step as well as the cyclative release step are also presented.

Original languageEnglish (US)
Pages (from-to)3081-3086
Number of pages6
JournalJournal of Organic Chemistry
Volume63
Issue number9
DOIs
StatePublished - May 1 1998

ASJC Scopus subject areas

  • Organic Chemistry

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