Stereoselective ring expansion of vinyl oxiranes: Mechanistic insights and natural product total synthesis

Matthew Brichacek, Lindsay A. Batory, Jon T Njardarson

Research output: Contribution to journalArticle

34 Citations (Scopus)

Abstract

"Chemical Equation Presented" What a (strain) relief! The first broadly applicable, catalytic, and stereoselective vinyl oxirane ring expansion is described (see scheme; hfacac = hexafluoroacetylacetonate). The stereoselectivity was influenced by several reaction parameters, and kinetic studies support a mechanistic proposal involving the in situ formation of a more reactive catalytic species. This ring-expansion reaction has been employed in the asymmetric total synthesis of (+)-goniothalesdiol.

Original languageEnglish (US)
Pages (from-to)1648-1651
Number of pages4
JournalAngewandte Chemie - International Edition
Volume49
Issue number9
DOIs
StatePublished - Feb 22 2010
Externally publishedYes

Fingerprint

Biological Products
Stereoselectivity
Kinetics
3,4-epoxy-1-butene
hexafluoroacetylacetonate
goniothalesdiol

Keywords

  • Copper
  • Natural products
  • Oxiranes
  • Stereoselectivity
  • Total synthesis

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis

Cite this

Stereoselective ring expansion of vinyl oxiranes : Mechanistic insights and natural product total synthesis. / Brichacek, Matthew; Batory, Lindsay A.; Njardarson, Jon T.

In: Angewandte Chemie - International Edition, Vol. 49, No. 9, 22.02.2010, p. 1648-1651.

Research output: Contribution to journalArticle

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