Preparation of γ,δ-unsaturated-β-ketoesters: Lewis acid-catalysed CH insertion of ethyl diazoacetate into α,β-unsaturated aldehydes

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Date
2017-07-29
Authors
Gandhi, Hirenkumar
O'Sullivan, Timothy P.
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Elsevier
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Abstract
The synthesis of γ,δ-unsaturated-β-keto esters was achieved by the Lewis acid-catalysed direct CH insertion of an α-diazoester into various α,β-substituted-unsaturated aldehydes. CH insertion of ethyl diazoacetate into alkyl- and aryl-substituted α,β-unsaturated aldehydes was performed under mild conditions to afford the corresponding γ,δ-unsaturated-β-keto esters in moderate to high yields as a mixture of keto/enol tautomers.
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γ , δ-Unsaturated-β-ketoesters , CH insertion , Ethyl diazoacetate
Citation
Gandhi, H. and O'Sullivan, T. P. (2017) 'Preparation of γ,δ-unsaturated-β-ketoesters: Lewis acid-catalysed CH insertion of ethyl diazoacetate into α,β-unsaturated aldehydes', Tetrahedron Letters, 58(36), pp. 3533-3535. doi: 10.1016/j.tetlet.2017.07.095