2-Aryl-5,5-bisoxazolin-2-yl[1,3]dioxanes as solution phase and immobilised ligands for highly enantioselective cyclopropanations

[Display omitted] 2-Aryl-5,5-bisoxazolin-2-yl[1,3]dioxanes 5, which can be easily prepared in three steps from diethyl bishydroxymethylmalonate, amino alcohol and an aromatic aldehyde, have been used for the copper catalysed asymmetric cyclopropanation of styrene with ethyl diazoacetate in up to 99%...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 2005-04, Vol.16 (8), p.1415-1418
Main Authors: Knight, Julian G., Belcher, Paul E.
Format: Article
Language:English
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Summary:[Display omitted] 2-Aryl-5,5-bisoxazolin-2-yl[1,3]dioxanes 5, which can be easily prepared in three steps from diethyl bishydroxymethylmalonate, amino alcohol and an aromatic aldehyde, have been used for the copper catalysed asymmetric cyclopropanation of styrene with ethyl diazoacetate in up to 99% ee for the trans-cyclopropane. Grafting onto a bromo-Wang resin produced an immobilised ligand 9 which gave the trans-cyclopropane in 65% ee.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2005.02.026