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 Lia, Xiang-Yu Chena, Qiang Liua, Anssi Peuronenb, Kari Rissanenb, Dieter Enders*a
  • aInstitute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   Email: enders@rwth-aachen.de
  • bDepartment of Chemistry, Nanoscience Center, University of Jyvaskyla, 40014 JYU, Finland
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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