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Silica sulfuric acid as a reusable heterogeneous catalyst for the diastereoselective Mukaiyama aldol reaction of 2-(trimethylsilyloxy)furan: facile synthesis of γ-butenolides

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Abstract

Silica sulfuric acid was found to be an efficient catalyst for the vinylogous Mukaiyama aldol reaction of 2-(trimethylsilyloxy)furan with various aldehydes with good diastereoselection. The reaction proceeds rapidly in THF, affording the corresponding 5-(arylhydroxymethyl)furan-2(5H)-ones in good yields. This method offers significant advantages such as experimental simplicity, and recoverability and reusability of the catalyst.

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Acknowledgments

M.N.P. thanks CSIR, New Delhi, for the award of a fellowship. M.R. thanks IICT, Hyderabad for providing facilities.

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Authors and Affiliations

  1. Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad, 500 007, India

    Gowravaram Sabitha, M. Nagendra Prasad, M. Ramesh & J. S. Yadav

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  1. Gowravaram Sabitha
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  2. M. Nagendra Prasad
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  3. M. Ramesh
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  4. J. S. Yadav
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Correspondence to Gowravaram Sabitha.

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Sabitha, G., Nagendra Prasad, M., Ramesh, M. et al. Silica sulfuric acid as a reusable heterogeneous catalyst for the diastereoselective Mukaiyama aldol reaction of 2-(trimethylsilyloxy)furan: facile synthesis of γ-butenolides. Monatsh Chem 141, 1245–1248 (2010). https://doi.org/10.1007/s00706-010-0388-z

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  • DOI: https://doi.org/10.1007/s00706-010-0388-z

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