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Synthesis 2017; 49(08): 1808-1815
DOI: 10.1055/s-0036-1588381
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© Georg Thieme Verlag Stuttgart · New York

Asymmetric Synthesis of Five-Membered Spiropyrazolones via N-Heterocyclic Carbene (NHC)-Catalyzed [3+2] Annulations

Sun Li
a   Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany
,
Lei Wang
a   Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany
,
Pankaj Chauhan
a   Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany
,
Anssi Peuronen
b   Department of Chemistry, Nanoscience Center, University of Jyvaskyla, 40014 JYU, Finland   Email: enders@rwth-aachen.de
,
Kari Rissanen
b   Department of Chemistry, Nanoscience Center, University of Jyvaskyla, 40014 JYU, Finland   Email: enders@rwth-aachen.de
,
Dieter Enders*
a   Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany
› Author Affiliations
Further Information

Publication History

Received: 25 November 2016

Accepted: 29 November 2016

Publication Date:
20 December 2016 (online)

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Abstract

A new synthetic strategy for the asymmetric synthesis of five-membered spiropyrazolones via N-heterocyclic carbene-catalyzed [3+2] annulations employing enals and unsaturated pyrazolones as substrates has been developed. The new protocol allows the flexible variation of all four substituents of the pharmaceutically important spiropyrazolones in moderate to very good yields and in most cases with excellent diastereoselectivities and good to excellent enantioselectivities.

Key words

asymmetric synthesis - spiropyrazolone - N-heterocyclic carbine - organocatalysis - [3+2] cycloaddition

Supporting Information

    Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588381.
  • Supporting Information
 

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