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Chemistry of Heterocyclic Compounds

, Volume 54, Issue 3, pp 320–328 | Cite as

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

  • Nadine Muschelknautz
  • Frank Rominger
  • Thomas J. J. MüllerEmail author
Article
  • 138 Downloads

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.

Keywords

furanones rhodium tetrahydrofurans asymmetric catalysis cycloisomerization homogeneous catalysis hydrogenation one-pot reactions sequential catalysis 

Notes

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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© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • Nadine Muschelknautz
    • 1
  • Frank Rominger
    • 2
  • Thomas J. J. Müller
    • 1
    Email author
  1. 1.Institut für Organische Chemie und Makromolekulare Chemie, Lehrstuhl für Organische ChemieHeinrich-Heine-Universität DüsseldorfDüsseldorfGermany
  2. 2.Organisch-Chemisches InstitutRuprecht-Karls-Universität HeidelbergHeidelbergGermany

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