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Diazo Compounds and Phenyliodonium Ylides in Inter- and Intramolecular Cyclopropanations Catalyzed by Dirhodium(II). Synthesis and Chiral Resolution by GC versus HPLC

Citation

Ghanem, A and Lacrampe, F and Aboul-Enein, HY and Schurig, V, Diazo Compounds and Phenyliodonium Ylides in Inter- and Intramolecular Cyclopropanations Catalyzed by Dirhodium(II). Synthesis and Chiral Resolution by GC versus HPLC, Monatshefte fur Chemie / Chemical Monthly, 136, (7) pp. 1205-1219. ISSN 0026-9247 (2005) [Refereed Article]


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The original publication is available at www.springerlink.com

Official URL: http://www.springerlink.com

DOI: doi:10.1007/s00706-005-0299-6

Abstract

The dirhodium(II)-catalyzed intermolecular cyclopropanation of a set of olefins with either diazo free phenyliodonium ylides or diazo compounds afforded cyclopropanes derived from Meldrum’s acid, dimethyl malonate, (silanoxyvinyl)diazoacetates, 3,3,3-trifluoro-2-diazopropionate, ethyl diazo(triethyl)- and (dimethylphenyl)silylacetate with moderate to high yield in either racemic or enantio-enriched forms. The intramolecular cyclopropanation of triethylsilyl-substituted allyl diazoacetates in the presence of the chiral rhodium(II) catalyst [Rh2(s-nttl)4] in toluene afforded the corresponding cyclopropanes with up to 37% ee. An efficient chiral separation method based on enantioselective GC and HPLC was developed. The method provides information about the chemical yields of the cyclopropane products, enantioselectivity, substrate specifity, and catalytic activity of the chiral catalysts used in the inter- and intramolecular cyclopropanation reactions and avoids time-consuming work-up procedures.

Item Details

Item Type:Refereed Article
Keywords:Catalysts; Chiral resolution; Cyclopropanes; Gas chromatography; High performance liquid chromatography.
Research Division:Chemical Sciences
Research Group:Organic Chemistry
Research Field:Organic Chemical Synthesis
Objective Division:Expanding Knowledge
Objective Group:Expanding Knowledge
Objective Field:Expanding Knowledge in the Chemical Sciences
Author:Ghanem, A (Dr Ashraf Ghanem)
ID Code:58304
Year Published:2005
Web of Science® Times Cited:11
Deposited By:Austn Centre for Research in Separation Science
Deposited On:2009-09-25
Last Modified:2010-04-13
Downloads:0

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