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Asymmetric cyclopropanations and cycloadditions of dioxocarbenes


Muller, P and Allenbach, YF and Chappellet, S and Ghanem, A, Asymmetric cyclopropanations and cycloadditions of dioxocarbenes, Synthesis, 2006, (10) pp. 1689-1696. ISSN 0039-7881 (2006) [Refereed Article]

DOI: doi:10.1055/s-2006-926452


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. © Georg Thieme Verlag Stuttgart.

Item Details

Item Type:Refereed Article
Research Division:Chemical Sciences
Research Group:Analytical chemistry
Research Field:Separation science
Objective Division:Expanding Knowledge
Objective Group:Expanding knowledge
Objective Field:Expanding knowledge in the chemical sciences
UTAS Author:Ghanem, A (Dr Ashraf Ghanem)
ID Code:58423
Year Published:2006
Web of Science® Times Cited:33
Deposited By:Austn Centre for Research in Separation Science
Deposited On:2009-10-02
Last Modified:2009-10-02

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