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Asymmetric cyclopropanations and cycloadditions of dioxocarbenes

Chappellet, Sabrina
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 CarbenoidsCatalysisDiazo decompositionPhenyl­iodonium ylidesRhodium
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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

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Deposited on : 2010-06-18

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