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

71 Citations (Scopus)

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

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Carbanilides
Hydantoins
Cycloaddition
Cyclization
Proline
Imidazoles
Stereoselectivity
Die casting inserts
Functional groups
Resins
Experiments
azomethine

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Solid-phase synthesis : Intramolecular azomethine ylide cycloaddition (→proline) and carbanilide cyclization (→hydantoin) reactions. / Gong, Young Dae; Najdi, Samir; Olmstead, Marilyn M.; Kurth, Mark J.

In: Journal of Organic Chemistry, Vol. 63, No. 9, 01.05.1998, p. 3081-3086.

Research output: Contribution to journalArticle

Gong, Young Dae ; Najdi, Samir ; Olmstead, Marilyn M. ; Kurth, Mark J. / Solid-phase synthesis : Intramolecular azomethine ylide cycloaddition (→proline) and carbanilide cyclization (→hydantoin) reactions. In: Journal of Organic Chemistry. 1998 ; Vol. 63, No. 9. pp. 3081-3086.
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