Synthesis 2017; 49(21): 4861-4868
DOI: 10.1055/s-0036-1588509
paper
© Georg Thieme Verlag Stuttgart · New York

N-Heterocyclic Carbene-Catalyzed Activation of α-Chloroaldehydes: Asymmetric Synthesis of 5-Cyano-Substituted Dihydropyranones

Sun Li
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   Email: enders@rwth-aachen.de
,
Xiang-Yu Chen
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   Email: enders@rwth-aachen.de
,
Qiang Liu
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   Email: enders@rwth-aachen.de
,
Anssi Peuronen
Department of Chemistry, Nanoscience Center, University of Jyvaskyla, 40014 JYU, Finland
,
Kari Rissanen
Department of Chemistry, Nanoscience Center, University of Jyvaskyla, 40014 JYU, Finland
,
Dieter Enders*
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   Email: enders@rwth-aachen.de
› Author Affiliations
Financial support from the European Research Council (ERC Advanced Grant 320493, ‘DOMINOCAT’) is gratefully acknowledged.
Further Information

Publication History

Received: 26 June 2017

Accepted: 26 June 2017

Publication Date:
26 July 2017 (eFirst)

Abstract

An N-heterocyclic carbene (NHC)-catalyzed asymmetric [4+2] annulation of (E)-2-benzoyl-3-phenylacrylonitriles with α-chloroaldehydes has been developed. The protocol leads to 5-cyano-substituted dihydropyranones in good to excellent yields with excellent diastereo- and enantioselectivities (up to 93% yield, >20:1 d.r. and 99% ee).

Supporting Information

 
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