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

초록

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-[(I-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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