Acid-Catalyzed Skeletal Reorganization of Phenyloxirane Derivatives
Chayamon Chantana1, Bundet Boekfa2, Jumreang Tummatorn3,1
1Program on Chemical Sciences, Chulabhorn Graduate Institute, Center of Excellence on Environmental Health and Toxicology (EHT), Office of Permanent Secretary (OPS), Ministry of Higher Education, Science, Research and Innovation (MHESI), 54 Kamphaeng Phet 6, Laksi, Bangkok 10210, Thailand.
Abstract:
This work demonstrates acid-promoted skeletal reorganization of oxirane derivatives to afford complex skeletons. 2-(2-(Oxiran-2-yl)benzyl)furans gave benzo-fused tricyclic products through a highly diastereoselective intramolecular [3+2] cycloaddition. In contrast, ortho-alkynylphenyl oxiranes underwent skeletal rearrangement under Brønsted and Lewis acid conditions to give indenylfuran and indanylbenzofuran frameworks, respectively. The transformations proceeded under mild conditions with broad substrate tolerance and were generally insensitive to electronic effects.
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