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Issue 31, 2019
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Stereoselective synthesis of hexahydrofuro[3,4-b]furan-4-ol and its dimer via tandem Prins and pinacol rearrangement

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Abstract

A novel synthetic route for the cyclization of ((4S,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)methanol with aldehydes to give hexahydrofuro[3,4-b]furan-4-ol and its dimer was developed. A variety of substituted furanol (up to 86%) and its bis-derivatives were obtained in good yields (up to 66%) with excellent diastereo- and enantio-selectivity mediated by borontrifluoride etherate. The dimer was conveniently converted into its corresponding monomer using aqueous zinc(II) chloride in THF in quantitative yields.

Graphical abstract: Stereoselective synthesis of hexahydrofuro[3,4-b]furan-4-ol and its dimer via tandem Prins and pinacol rearrangement

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Publication details

The article was received on 14 Jun 2019, accepted on 18 Jul 2019 and first published on 18 Jul 2019


Article type: Paper
DOI: 10.1039/C9OB01353A
Org. Biomol. Chem., 2019,17, 7398-7407

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    Stereoselective synthesis of hexahydrofuro[3,4-b]furan-4-ol and its dimer via tandem Prins and pinacol rearrangement

    S. Shit, N. Devi, N. R. Devi and A. K. Saikia, Org. Biomol. Chem., 2019, 17, 7398
    DOI: 10.1039/C9OB01353A

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