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Asymmetric cyclopropanations and cycloadditions of dioxocarbenes
Citation
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
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 [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 |
| Author: | Ghanem, A (Dr Ashraf Ghanem) |
| ID Code: | 58423 |
| Year Published: | 2006 |
| Web of Science® Times Cited: | 29 |
| Deposited By: | Austn Centre for Research in Separation Science |
| Deposited On: | 2009-10-02 |
| Last Modified: | 2009-10-02 |
| Downloads: | 0 |
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