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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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.

키워드

1,3-butadien-2-ylationazetidinonescatalysisDiels-Alder reactionsindiumTRICYCLIC BETA-LACTAMSASYMMETRIC-SYNTHESIS4-SUBSTITUTED 2-AZETIDINONESSTEREOSELECTIVE ALLYLATIONSTEREOCONTROLLED SYNTHESISBUILDING-BLOCKSSYNTHON METHODAQUEOUS-MEDIA4-OXOAZETIDINE-2-CARBALDEHYDES4-(2-PROPYNYL)AZETIDINONES
제목
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
저자
Lee, KooyeonLee, Phil Ho
DOI
10.1002/chem.200700796
발행일
2007
유형
Article
저널명
Chemistry - A European Journal
13
31
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8877 ~ 8883