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

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

Received: 23. März 2018

Accepted: 28. März 2018

Publikationsdatum:
03. Mai 2018 (online)


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