Synthesis 2018; 50(13): 2523-2532
DOI: 10.1055/s-0036-1591995
paper
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Synthesis of Cyclopentene-Fused Tetrahydroquinolines via N-Heterocyclic Carbene Catalyzed Domino Reactions

Autoren

  • Long Zhao

    Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   eMail: enders@rwth-aachen.de
  • Sun Li

    Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   eMail: enders@rwth-aachen.de
  • Lei Wang

    Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   eMail: enders@rwth-aachen.de
  • Shun Yu

    Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   eMail: enders@rwth-aachen.de
  • Gerhard Raabe

    Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   eMail: enders@rwth-aachen.de
  • Dieter Enders  *

    Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   eMail: enders@rwth-aachen.de
Weitere Informationen

Publikationsverlauf

Received: 23. März 2018

Accepted: 28. März 2018

Publikationsdatum:
03. Mai 2018 (online)


Graphical Abstract

Abstract

A new strategy for the N-heterocyclic carbene catalyzed asymmetric synthesis of cyclopentene-fused tetrahydroquinoline derivatives has been developed. The one-pot organocatalytic domino protocol allows a direct entry to the characteristic cyclopenta[c]tetrahydroquinoline core of many alkaloids and some potential drugs employing readily available quinolinone and enal substrates in good domino yields and stereoselectivities.

Supporting Information