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Synfacts 2009(12): 1404-1404  
DOI: 10.1055/s-0029-1218212
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

NHC-Catalyzed Intramolecular Hydroacylation of Unactivated Double Bonds

Contributor(s): Benjamin List, Steffen Müller
K. Hirano, A. T. Biju, I. Piel, F. Glorius*
Westfälische Wilhelms-Universität Münster, Germany
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Publication History

Publication Date:
20 November 2009 (online)

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Significance

Thiazolium salt 1 derived N-heterocyclic carbene was found to efficiently promote the hydroacylation of unactivated double bonds. In the presence of 1 and DBU several aromatic ortho-allyloxy aldehydes reacted to the corresponding chromanones in good to excellent yields (up to 96%). The method is compatible with different functional groups on the aromatic ring and differently substituted allyl moieties, leading to all-carbon quaternary stereocenters. Finally also a ­dihydroquinolinone was successfully synthesized using this new reaction. Mechanistically a certain similarity to the Conia-ene reactions has been ­noticed by the authors.

Review: D. Enders, O. Niemeier, A. Henseler Chem. Rev. 2007, 107, 5606-5655.