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Scientific article
English

Asymmetric cyclopropanations and cycloadditions of dioxocarbenes

Published inSynthesis, no. 10, p. 1689-1696
Publication date2006
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 [Rh2{(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 (silyloxy­-vinyl)diazoacetate. Enantioselective dipolar cycloadditions of diazo­pyruvate to polar olefins have been realized with Ru(II)-pybox catalysts.

Keywords
  • Carbenoids
  • Catalysis
  • Diazo decomposition
  • Phenyl­iodonium ylides
  • Rhodium
Citation (ISO format)
MULLER, Paul et al. Asymmetric cyclopropanations and cycloadditions of dioxocarbenes. In: Synthesis, 2006, n° 10, p. 1689–1696. doi: 10.1055/s-2006-926452
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ISSN of the journal0039-7881
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