Oxetan-3-ols as 1,2-bis-Electrophiles in a Brønsted-Acid-Catalyzed Synthesis of 1,4-Dioxanes.

Autor: Rojas JJ; Department of Chemistry, Imperial College London, Molecular Sciences Research Hub, White City Campus, Wood Lane, London W12 0BZ, U.K., Torrisi E; Department of Chemistry, Imperial College London, Molecular Sciences Research Hub, White City Campus, Wood Lane, London W12 0BZ, U.K.; Department of Biomolecular Sciences, School of Pharmacy, University of Urbino 'Carlo Bo', P.za Rinascimento, 6, 61029 Urbino (PU), Italy., Dubois MAJ; Department of Chemistry, Imperial College London, Molecular Sciences Research Hub, White City Campus, Wood Lane, London W12 0BZ, U.K., Hossain R; Department of Chemistry, Imperial College London, Molecular Sciences Research Hub, White City Campus, Wood Lane, London W12 0BZ, U.K., White AJP; Department of Chemistry, Imperial College London, Molecular Sciences Research Hub, White City Campus, Wood Lane, London W12 0BZ, U.K., Zappia G; Department of Biomolecular Sciences, School of Pharmacy, University of Urbino 'Carlo Bo', P.za Rinascimento, 6, 61029 Urbino (PU), Italy., Mousseau JJ; Pfizer Worldwide Research, Development and Medical, Eastern Point Road, Groton, Connecticut 06340, United States., Choi C; Pfizer Worldwide Research, Development and Medical, Eastern Point Road, Groton, Connecticut 06340, United States., Bull JA; Department of Chemistry, Imperial College London, Molecular Sciences Research Hub, White City Campus, Wood Lane, London W12 0BZ, U.K.
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2022 Apr 01; Vol. 24 (12), pp. 2365-2370. Date of Electronic Publication: 2022 Mar 21.
DOI: 10.1021/acs.orglett.2c00568
Abstrakt: Annulations that combine diacceptors with bis-nucleophiles are uncommon. Here, we report the synthesis of 1,4-dioxanes from 3-aryloxetan-3-ols, as 1,2-bis-electrophiles and 1,2-diols. Brønsted acid Tf 2 NH catalyzes both the selective activation of the oxetanol, to form an oxetane carbocation that reacts with the diol, and intramolecular ring opening of the oxetane. High regio- and diastereoselectivity are achieved with unsymmetrical diols. The substituted dioxanes and fused bicyclic products present interesting motifs for drug discovery and can be further functionalized.
Databáze: MEDLINE
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