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Intramolecular Diels-Alder reaction of 2-diphenylphosphinyl-5-(propargyloxymethyl)furans followed by nucleophilic 1,2-rearrangement of the phosphinyl group |
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| Authors: | Hsien-Jen Wu Chuan-Fang Liu Hui-Chang Lin |
| Institution: | a Department of Applied Chemistry, National Chiao Tung University, Hsinchu, Taiwan b Department of Medical Technology, Yuanpei University, Hsinchu, Taiwan c Graduate Institute of Pharmaceutical Chemistry, China Medical University, Taichung, Taiwan |
| Abstract: | The base-catalyzed intramolecular Diels-Alder reactions of 2-diphenylphosphinyl-5-(propargyloxymethyl)furans 2a-e gave the tetrahydrofuran ring annulated o-diphenylphosphinophenols 3a-e in 70-80% yields, a novel reaction involving an intramolecular Diels-Alder reaction of furan diene with allenyl ether dienophile followed by a nucleophilic 1,2-rearrangement of the diphenylphosphinyl group. |
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