Study of substrate dependence on the diastereoselectivity of the ruthenium(II) porphyrin catalyzed tandem formation and 1,3-dipolar cycloaddition reactions of carbonyl ylides

Cong Ying Zhou, Philip Wai Hong Chan, Wing Yiu Yu, Chi Ming Che

Research output: Journal article publicationJournal articleAcademic researchpeer-review

21 Citations (Scopus)

Abstract

The effect of substrate substitution on reaction selectivity for the ruthenium(II) porphyrin catalyzed tandem carbonyl ylide formation/1,3-dipolar cycloaddition reaction of a variety of alkyl and aryl substituted α-diazo ketones 1 with π-unsaturated compounds was examined. The results suggested the diastereoselectivity of the reaction to be highly substrate dependant. Similar yields and cis/trans selectivities have also been achieved for the analogous reactions with rhodium(II,II) dimer as catalyst.
Original languageEnglish
Pages (from-to)1403-1412
Number of pages10
JournalSynthesis
Issue number9
Publication statusPublished - 22 Jul 2003
Externally publishedYes

Keywords

  • 1,3-dipolar cycloaddition
  • Carbonyl ylide formation
  • Metallocarbenoids
  • Rhodium(II,II) dimers
  • Ruthenium(II) porphyrins

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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