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Sequentially rhodium-catalyzed enantioselective cycloisomerization–hydrogenation syntheses of alkylidene butyrolactone β-hydroxyethanes and alkylidene tetrahydrofuran β-aminoethanes

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Chemistry of Heterocyclic Compounds Aims and scope

The enantioselective Rh-catalyzed Alder-ene cycloisomerization of ester- and ether-tethered alkyne allyl alcohols is an excellent entry to subsequent Rh-catalyzed one-pot hydrogenations in the sense of sequentially Rh-catalyzed processes to chiral alkylidene butyrolactone β-hydroxyethanes and alkylidene tetrahydrofuran β-aminoethanes, respectively, with excellent levels of enantioselectivity.

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Financial support of the Deutsche Forschungsgemeinschaft (SFB 623) and Fonds der Chemischen Industrie is gratefully acknowledged. We also cordially thank the BASF SE for the generous donation of chemicals.

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Authors and Affiliations

  1. Institut für Organische Chemie und Makromolekulare Chemie, Lehrstuhl für Organische Chemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstraße 1, D-40225, Düsseldorf, Germany

    Nadine Muschelknautz & Thomas J. J. Müller

  2. Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, D-69120, Heidelberg, Germany

    Frank Rominger

Authors
  1. Nadine Muschelknautz
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  2. Frank Rominger
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  3. Thomas J. J. Müller
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Correspondence to Thomas J. J. Müller.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2018, 54(3), 320–328

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Muschelknautz, N., Rominger, F. & Müller, T.J.J. Sequentially rhodium-catalyzed enantioselective cycloisomerization–hydrogenation syntheses of alkylidene butyrolactone β-hydroxyethanes and alkylidene tetrahydrofuran β-aminoethanes. Chem Heterocycl Comp 54, 320–328 (2018). https://doi.org/10.1007/s10593-018-2267-1

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  • DOI: https://doi.org/10.1007/s10593-018-2267-1

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