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unige:6937 
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Asymmetric cyclopropanations and cycloadditions of dioxocarbenes |
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| 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 | |
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| 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 https://archive-ouverte.unige.ch/unige:6937 |
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