The rhodium-catalyzed carbene cyclization cycloaddition cascade reaction of vinylsulfonates

Bairu Shi, Sandra Merten, David K.Y. Wong, John C.K. Chu, Lok Lok Liu, Sze Kui Lam, Anne Jäger, Wing Tak Wong, Pauline Chiu, Peter Metz

Research output: Journal article publicationJournal articleAcademic researchpeer-review

32 Citations (Scopus)

Abstract

Vinylsulfonates have proved to be excellent dipolarophiles for carbonyl ylides derived from diazoketones in rhodium-catalyzed intramolecular cycloadditions. Polyfunctional substrates, such as 8 and (+)-15, were readily available from hydroxy esters, e.g. 1 and the cyclopenta-1,3-dione 10, respectively, and the resulting polycyclic sultones were formed under mild reaction conditions in high yields with very good diastereoselectivities. A ruthenium-catalyzed asymmetric transfer hydrogenation was found to desymmetrize the meso-cyclopenta-1,3-dione 12 efficiently. KGaA, Weinheim.
Original languageEnglish
Pages (from-to)3128-3132
Number of pages5
JournalAdvanced Synthesis and Catalysis
Volume351
Issue number18
DOIs
Publication statusPublished - 1 Jan 2009
Externally publishedYes

Keywords

  • Asymmetric reduction
  • Cycloaddition
  • Domino reactions
  • Sulfur heterocycles
  • Transition metal catalysis

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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