Indium-mediated selective introduction of a 1,3-butadien-2-yl group at the C4-position in 2-azetidinones and application of 1,3-diene-tethered 2-azetidinones in the Diels-Alder reaction |
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| Authors: | Lee Kooyeon Lee Phil Ho |
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| Affiliation: | National Research Laboratory of Catalytic Organic Reaction, Department of Chemistry and Institute for Basic Science, Kangwon National University, Chunchon 200-701, Republic of Korea. |
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| Abstract: | The reaction of 4-acetoxy-2-azetidinones with organoindium reagents generated in situ from indium and 1,4-dibromo-2-butyne in the presence of LiCl in DMF selectively produced 2-azetidinones which contain a 1,3-butadienyl-2-yl group at the C4-position in good yields. The Diels-Alder reaction of 4-[(1-methylene)prop-2-enyl]-2-azetidinones with a variety of dienophiles provided 2-azetidinones with valuable functional-group-substituted six-membered rings at the C4-position in good yields. |
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| Keywords: | 1,3‐butadien‐2‐ylation azetidinones catalysis Diels–Alder reactions indium |
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