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Highly stereoselective metal-mediated domino aldol reactions of propiophenone enolates with heteroaromatic, aliphatic, and unsaturated aldehydes

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Abstract

The one-pot reaction of propiophenone with heteroaromatic, aliphatic, and unsaturated aldehydes in the presence of metal halides furnishes racemic tetrahydro-2H-pyran-2,4-diols in a highly diastereo-selective manner. The mechanism for the stereoselective product formation as well as the surprising formation of a side product was explained on the basis of DFT computations.

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Acknowledgments

Financial support from the DFG (Graduiertenkolleg, SFB) and the Fonds der Chemischen Industrie is gratefully acknowledged. We are grateful to Dr. Thomas Koy and Wolfgang Henn for their valuable preparative work and helpful discussions in the early stage of this manuscript. We are indebted to the High-Performance-Computing (HPC) Linux Cluster HorUS of the University of Siegen for computational support.

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Authors and Affiliations

  1. Department Chemie-Biologie, Universität Siegen, Adolf-Reichwein-Str. 2, 57068, Siegen, Germany

    M. Emin Cinar & Michael Schmittel

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  1. M. Emin Cinar
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  2. Michael Schmittel
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Correspondence to M. Emin Cinar or Michael Schmittel.

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Cinar, M.E., Schmittel, M. Highly stereoselective metal-mediated domino aldol reactions of propiophenone enolates with heteroaromatic, aliphatic, and unsaturated aldehydes. Monatsh Chem 147, 1925–1932 (2016). https://doi.org/10.1007/s00706-016-1841-4

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  • DOI: https://doi.org/10.1007/s00706-016-1841-4

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