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  • Title: 2,5-cis-2,3,5-Trisubstituted tetrahydrofurans from the diastereomixture of 2,4-disubstituted 1,3-dioxepins via stereomutation.
    Author: Kubo O, Yahata K, Maegawa T, Fujioka H.
    Journal: Chem Commun (Camb); 2011 Aug 28; 47(32):9197-9. PubMed ID: 21748169.
    Abstract:
    A diastereoselective ring contraction of the diastereomixture of 2,4-disubstituted 1,3-dioxepins to 2,5-cis-2,3,5-trisubstituted tetrahydrofurans was achieved using TfOH in DMF. The reaction appears to proceed via a chair-like transition state, in which stereomutation of the oxocarbenium occurred, followed by an aldol-type cyclization.
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