Asymmetric cyclopropanations and cycloadditions of dioxocarbenes

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Title		Asymmetric cyclopropanations and cycloadditions of dioxocarbenes
Authors		Muller, Paul Allenbach, Yves Chappellet, Sabrina Ghanem Abdallah, Ashraf
Published in		Synthesis. 2006, no. 10, p. 1689-1696
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
Identifiers		DOI: 10.1055/s-2006-926452
Full text		Article - Limited access to UNIGE
Structures		Faculté des sciences / Section de chimie et biochimie / Département de chimie organique
Citation (ISO format)		MULLER, Paul et al. Asymmetric cyclopropanations and cycloadditions of dioxocarbenes. In: Synthesis, 2006, n° 10, p. 1689-1696. https://archive-ouverte.unige.ch/unige:6937