SEQUENTIALLY RHODIUM-CATALYZED ENANTIOSELECTIVE CYCLOISOMERIZATION–HYDROGENATION SYNTHESES OF ALKYLIDENE BUTYROLACTONE β-HYDROXYETHANES AND ALKYLIDENE TETRAHYDROFURAN β-AMINOETHANES

Authors

  • Nadine Muschelknautz Institut für Organische Chemie und Makromolekulare Chemie, Lehrstuhl für Organische Chemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstraße 1, D-40225 Düsseldorf
  • Frank Rominger Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, D-69120 Heidelberg
  • Thomas J. J. Müller Institut für Organische Chemie und Makromolekulare Chemie, Lehrstuhl für Organische Chemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstraße 1, D-40225 Düsseldorf

DOI:

https://doi.org/10.1007/4484

Keywords:

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

Abstract

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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Published

2018-05-16

Issue

Vol. 54 No. 3 (2018): Metal-catalyzed synthesis of heterocycles

Section

Original Papers