Stereoselective synthesis of functionalized pyrrolidines by ruthenium porphyrin-catalyzed decomposition of α-diazo esters and cascade azomethine ylide formation/1,3-dipolar cycloaddition reactions

Gong Yong Li, Jian Chen, Wing Yiu Yu, Wei Hong, Chi Ming Che

Research output: Journal article publicationJournal articleAcademic researchpeer-review

67 Citations (Scopus)

Abstract

(Matrix presented) Ruthenium porphyrins catalyze three-component coupling reaction of α-diazo esters with a series of N-benzylidene imines and alkenes to form functionalized pyrrolidines in excellent diastereoselectivities. The reaction proceeds via a reactive ruthenium-carbene intermediate and its subsequent reaction with imine to generate azomethine ylide, which reacts with alkenes via 1,3-diploar cycloaddition.
Original languageEnglish
Pages (from-to)2153-2156
Number of pages4
JournalOrganic Letters
Volume5
Issue number12
DOIs
Publication statusPublished - 12 Jun 2003
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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