An N‑Heterocyclic Carbene-Mediated, Enantioselective and Multicatalytic Strategy to Access Dihydropyranones in a Sequential Three-Component One-Pot Reaction

The multicatalytic generation of 3,5,6-trisubstituted 3,4-dihydropyranones with high enantioselectivity using a highly convergent strategy starting from commercially available precursors is reported. The operationally simple three-step, one-pot protocol merges H-bond and NHC catalysis to provide cru...

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Bibliographic Details
Published in:Organic letters 2017-11, Vol.19 (22), p.6076-6079
Main Authors: Fuchs, Patrick J. W., Zeitler, Kirsten
Format: Article
Language:English
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Summary:The multicatalytic generation of 3,5,6-trisubstituted 3,4-dihydropyranones with high enantioselectivity using a highly convergent strategy starting from commercially available precursors is reported. The operationally simple three-step, one-pot protocol merges H-bond and NHC catalysis to provide crucial, reactive β-unsubstituted enones from nitroalkenes as latent 1,2-biselectrophiles. These intermediates are directly funneled into a further NHC-catalyzed formal hetero-Diels–Alder reaction to deliver manifold chiral C(4)-unsubstituted dihydropyranones (typical ee >98%), allowing aliphatic and heteroaromatic substituents and hence expanding the scope of this Michael addition/lactonization.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b02889