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Oxetanyl Trichloroacetimidates Enable a General Synthesis of 3-Aryloxetane 3-carboxylic Acids
Xian Xiao1, Xiaocheng Wang1, Hai-Jun Zhang1
1State Key Laboratory of Precision and Intelligent Chemistry, Department of Chemistry, University of Science and Technology of China, Hefei, Anhui230026, China.
Abstract:
3-Aryloxetane 3-carboxylic acids are valuable medicinal chemistry building blocks but remain considerably less accessible and more costly than common oxetane feedstocks. Herein, we report a general synthesis of these compounds from readily available oxetanyl trichloroacetimidate (OTA) reagents. Friedel-Crafts trapping of oxetanyl carbocations generated from OTAs with inexpensive, biomass-derived 2-methylfuran, followed by selective oxidative cleavage of the resulting intermediates, furnishes a broad range of 3-aryloxetane 3-carboxylic acids. Electron-deficient, -neutral, and -rich arenes are all accommodated.
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