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Updated: Feb 27, 2026
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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
A Direct Synthesis of Highly Substituted π-Rich Aromatic Heterocycles from Oxetanes
Alexander R White1, Ryan A Kozlowski1, Shiou-Chuan Tsai2
1Department of Chemistry, University of California, Irvine, CA, 92697-2025, USA.
Abstract:
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.
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