Ruthenium porphyrin catalyzed intramolecular carbenoid C-H insertion. Stereoselective synthesis of Cis-disubstituted oxygen and nitrogen heterocycles

Wai Hung Cheung, Shi Long Zheng, Wing Yiu Yu, Guo Chuan Zhou, Chi Ming Che

Research output: Journal article publicationJournal articleAcademic researchpeer-review

105 Citations (Scopus)

Abstract

(Matrix presented) A ruthenium porphyrin-catalyzed stereoselective intramolecular carbenoid C-H insertion is described. Using [RuII(TTP)(CO)] as catalyst, aryl tosylhydrazones are converted to 2,3-dihydrobenzofurans, 2,3-dihydroindoles, and β-lactams in good yields and remarkable cis selectivity (up to 99%). Enantioselective synthesis of 2,3-dihydrobenzofurans is also achieved with [RuII(D4-Por*)(CO)] as catalyst, and up to 96% ee is attained.
Original languageEnglish
Pages (from-to)2535-2538
Number of pages4
JournalOrganic Letters
Volume5
Issue number14
DOIs
Publication statusPublished - 10 Jul 2003
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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