Intramolecular ionic Diels-Alder reactions of alpha-acetylenic acetals |
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| Authors: | Shim Seung-Bo Ko Yoon-Joo Yoo Byeong-Wook Lim Chang-Keun Shin Jung-Hyu |
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| Institution: | School of Chemistry, Seoul National University, Seoul 151-742, Korea. |
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| Abstract: | The intramolecular ionic Diels-Alder reaction of alpha-acetylenic acetals as a precursor of the propargyl cation has been investigated in the presence of Lewis acids and in protic acids. The reaction of diene-tethered alpha-acetylenic acetals (1-2) with formic acid yielded the regioselective intramolecular ionic Diels-Alder reaction products, bicyclodienal (9) and bicyclodienone (11) derivatives, in good yields. |
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