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Angew Chem Int Ed Engl. 2017 Aug 21;56(35):10525-10529. doi: 10.1002/anie.201704119. Epub 2017 Jul 21.

A Direct Synthesis of Highly Substituted π-Rich Aromatic Heterocycles from Oxetanes.

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Department of Chemistry, University of California, Irvine, CA, 92697-2025, USA.
Departments of Chemistry and of Molecular Biology & Biochemistry, University of California, Irvine, CA, 92697-2025, USA.


The ubiquitous use of π-rich five-membered heterocycles has driven the development of new methods for their synthesis for more than a century. Here, we disclose a general and reliable reaction manifold for the construction of highly substituted heterocycles through a facile Lewis-acid-catalyzed oxetane rearrangement. Notably, this methodology employs a keto-oxetane motif as a 1,4-dicarbonyl surrogate, which can be synthesized using robust alkylation or alkenylation reactions, and thus obviates the need to access 1,4-dicarbonyl compounds via umpoled starting materials. We harnessed this reactivity to generate a broad range of substituted furans and pyrroles, and extended this methodology to produce benzo-fused versions thereof.


cyclization; furans; heterocycles; oxetanes; strained rings


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