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Synthesis 2017; 49(21): 4861-4868
DOI: 10.1055/s-0036-1588509
DOI: 10.1055/s-0036-1588509
paper
N-Heterocyclic Carbene-Catalyzed Activation of α-Chloroaldehydes: Asymmetric Synthesis of 5-Cyano-Substituted Dihydropyranones
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 (online)
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).
Key words
dihydropyranones - asymmetric synthesis - organocatalysis - N-heterocyclic carbenes - α-chloroaldehydesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588509.
- Supporting Information
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