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

Lookup NU author(s): Dr Julian Knight

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Abstract

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. © 2005 Elsevier Ltd. All rights reserved.


Publication metadata

Author(s): Knight JG, Belcher PE

Publication type: Article

Publication status: Published

Journal: Tetrahedron Asymmetry

Year: 2005

Volume: 16

Issue: 8

Pages: 1415-1418

Print publication date: 18/04/2005

ISSN (print): 0957-4166

ISSN (electronic): 1362-511X

Publisher: Elsevier

URL: http://dx.doi.org/10.1016/j.tetasy.2005.02.026

DOI: 10.1016/j.tetasy.2005.02.026


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