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One-pot synthesis and chiral analysis of cyclopropane derivatives
Citation
Ghanem, A and Aboul-Enein, HY and Muller, P, One-pot synthesis and chiral analysis of cyclopropane derivatives, Chirality , 17, (1) pp. 44-50. ISSN 0899-0042 (2005) [Refereed Article]
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Abstract
A user-friendly, one-pot procedure was developed to access racemic as well as enantiomerically enriched cyclopropanes. Thus, the cyclopropanation of olefin (3) was performed using Meldrum's acid (4) or dimethyl malonate (5) and diacetoxyiodobenzene PhI(OAc)2 (6) or iodosyl benzene PhI=O (7) for in situ generation and decomposition of the phenyliodonium ylide 1 and 2, respectively. The reaction proceeds well with 5 mol% of achiral rhodium (II)-catalyst [Rh2(OAc)4] and a 10-fold excess of olefin affording the cyclopropane derivates 10 and 11, respectively, with high yield. The system is compatible with chiral Rh(II)-catalysts 8 and 9 and an enantiomeric excess up to 66% was achieved. An effective baseline separation of the enantiomers of the resulting cyclopropane derivatives was achieved using gas chromatography on the chiral stationary phase Chirasil--dex.
Item Details
Item Type: | Refereed Article |
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Keywords: | asymmetric catalysis • carbene • chirasil--Dex • cyclopropane • enantiomeric excess • enantioselective gas chromatography • rhodium complexes • ylide |
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 |
UTAS Author: | Ghanem, A (Dr Ashraf Ghanem) |
ID Code: | 58297 |
Year Published: | 2005 |
Web of Science® Times Cited: | 31 |
Deposited By: | Austn Centre for Research in Separation Science |
Deposited On: | 2009-09-25 |
Last Modified: | 2009-09-25 |
Downloads: | 0 |
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