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High diversity on simple substrates: 1,4 dihalo-2-butenes and other difunctionalised allylic halides for copper-catalysed SN2' reactions

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Published in Chemistry - A European Journal. 2008, vol. 14, no. 34, p. 10615-10627
Abstract Enantioselective allylic alkylation with an organomagnesium reagent catalyzed by copper thiophene carboxylate (CuTC) was carried out on difunctionalized substrates, such as commercially available 1,4-dichloro-2-butene and 1,4-dibromo-2-butene, and on similar compounds of higher substitution pattern of the olefin for the formation of all-carbon chiral quaternary centers. The high regioselectivity obtained throughout the reactions favored good regiocontrol for the addition of phenyl Grignard reagents. Other difunctionalized substrates (allylic ethers and allylic alcohols) also underwent asymmetric SN2 substitution.
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PMID: 18924190
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FALCIOLA, Caroline Alexandra, ALEXAKIS, Alexandre. High diversity on simple substrates: 1,4 dihalo-2-butenes and other difunctionalised allylic halides for copper-catalysed SN2' reactions. In: Chemistry - A European Journal, 2008, vol. 14, n° 34, p. 10615-10627. https://archive-ouverte.unige.ch/unige:8105

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Deposited on : 2010-06-21

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