Allenyl azide cycloaddition chemistry. Synthesis of pyrrolidine-containing bicycles and tricycles via the possible intermediacy of azatrimethylenemethane species

Ken S. Feldman, Malliga R. Iyer

Research output: Contribution to journalArticle

37 Citations (Scopus)

Abstract

Thermolysis of 5-azidoallenes bearing a C(1) methyl group and either an aryl ring or an alkene on C(1) furnishes tricyclic (from the aryl substrates) or bicyclic (from the alkenyl substrates) pyrrolidine products following formal H-CN addition across an intermediate imine. High levels of diastereoselectivity are observed in all cases studied. This reaction cascade presumably passes through unobserved triazoline and azatrimethylenemethane diyl intermediates en route to product.

Original languageEnglish (US)
Pages (from-to)4590-4591
Number of pages2
JournalJournal of the American Chemical Society
Volume127
Issue number13
DOIs
StatePublished - Apr 6 2005

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Imines
Bicycles
Azides
Cycloaddition
Cycloaddition Reaction
Alkenes
Bearings (structural)
Thermolysis
Substrates
Olefins
pyrrolidine
azatrimethylenemethane

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

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Allenyl azide cycloaddition chemistry. Synthesis of pyrrolidine-containing bicycles and tricycles via the possible intermediacy of azatrimethylenemethane species. / Feldman, Ken S.; Iyer, Malliga R.

In: Journal of the American Chemical Society, Vol. 127, No. 13, 06.04.2005, p. 4590-4591.

Research output: Contribution to journalArticle

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