en
Scientific article
Open access
English

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

Published inMonatshefte für Chemie, vol. 136, no. 7, p. 1205-1219
Collection
  • Open Access - Licence nationale Springer 
Publication date2005
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.

Citation (ISO format)
GHANEM, Ashraf et al. Diazo Compounds and Phenyliodonium Ylides in Inter- and Intramolecular Cyclopropanations Catalyzed by Dirhodium(II). Synthesis and Chiral Resolution by GC versus HPLC. In: Monatshefte für Chemie, 2005, vol. 136, n° 7, p. 1205–1219. doi: 10.1007/s00706-005-0299-6
Main files (1)
Article (Published version)
accessLevelPublic
Identifiers
ISSN of the journal0026-9247
337views
239downloads

Technical informations

Creation01/29/2019 2:09:00 PM
First validation01/29/2019 2:09:00 PM
Update time03/15/2023 3:38:51 PM
Status update03/15/2023 3:38:51 PM
Last indexation01/17/2024 4:47:18 AM
All rights reserved by Archive ouverte UNIGE and the University of GenevaunigeBlack