Asymmetric cyclopropanations and cycloadditions of dioxocarbenes

Paul Müller, Yves Allenbach, Sabrina Chappellet, Ashraf Ghanem

Research output: Contribution to journalArticle

34 Citations (Scopus)

Abstract

Methods for enantioselective transfer of carbenes starting from precursors carrying two carbonyl groups have been elaborated. A one-pot procedure for olefin cyclopropanation with CH-acidic precursors via intermediate phenyliodonium ylides has been developed. The structure of the [Rh-2{(S)-nttl}4] catalyst was optimized to produce up to 98% ee in olefin cyclopropanations with dimethyl malonate or Meldrum's acid. Highly selective Rh(II)-catalyzed olefin cyclopropanations could be observed upon replacement of methyl diazoacetoacetate by methyl (silyloxyvinyl)diazoacetate. Enantioselective dipolar cycloadditions of diazopyruvate to polar olefins have been realized with Ru(II)-pybox catalysts
Original languageEnglish
Pages (from-to)1689-1696
Number of pages8
JournalSynthesis
Volume37
Issue number34
DOIs
Publication statusPublished - 2006
Externally publishedYes

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