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

Gandhi, Hirenkumar; O’Sullivan, Timothy P.

doi:10.1016/j.tetlet.2017.07.095

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Cited by 2 publications

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“…In order to investigate reaction scope, a library of linear, aliphatic γ,δ-unsaturated β-keto esters was initially prepared via the niobium chloride-catalysed C-H insertion of ethyl diazoacetate into the corresponding α,β-unsaturated aldehydes [55]. Additional substrates, including aromatic and branched aliphatic substrates, were synthesised using Wittig chemistry, several of which are novel (see page 5 of Supporting Information) [56].…”

Section: Resultsmentioning

confidence: 99%

Organocatalytic Asymmetric Peroxidation of γ,δ-Unsaturated β-Keto Esters—A Novel Route to Chiral Cycloperoxides

2023

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A methodology for the asymmetric peroxidation of γ,δ-unsaturated β-keto esters is presented. Using a cinchona-derived organocatalyst, the target δ-peroxy-β-keto esters were obtained in high enantiomeric ratios of up to 95:5. Additionally, these δ-peroxy esters can be readily reduced to chiral δ-hydroxy-β-keto esters without impacting the β-keto ester functionality. Importantly, this chemistry opens up a concise route to chiral 1,2-dioxolanes, a common motif in many bioactive natural products, via a novel P2O5-mediated cyclisation of the corresponding δ-peroxy-β-hydroxy esters.

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Section: Resultsmentioning

confidence: 99%