Oxetan-3-ols as 1,2-bis-Electrophiles in a Brønsted-Acid-Catalyzed Synthesis of 1,4-Dioxanes
Juan J. Rojas, Elena Torrisi, Maryne A. J. Dubois, Riashat Hossain, Andrew J. P. White, Giovanni Zappia, James J. Mousseau, Chulho Choi, James A. Bull
Abstract
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.
Topics & Concepts
OxetaneChemistryElectrophileNucleophileIntramolecular forceCarbocationBicyclic moleculeRing (chemistry)DiolCatalysisBrønsted–Lowry acid–base theoryStereochemistryCombinatorial chemistryAcid catalysisMedicinal chemistryOrganic chemistryFluorine in Organic ChemistrySynthesis and Catalytic ReactionsChemical Synthesis and Analysis