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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
- Lee, Kooyeon;
- Lee, Phil Ho
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14초록
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-ylation; azetidinones; catalysis; Diels-Alder reactions; indium; TRICYCLIC BETA-LACTAMS; ASYMMETRIC-SYNTHESIS; 4-SUBSTITUTED 2-AZETIDINONES; STEREOSELECTIVE ALLYLATION; STEREOCONTROLLED SYNTHESIS; BUILDING-BLOCKS; SYNTHON METHOD; AQUEOUS-MEDIA; 4-OXOAZETIDINE-2-CARBALDEHYDES; 4-(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, Kooyeon; Lee, Phil Ho
- 발행일
- 2007
- 유형
- Article
- 권
- 13
- 호
- 31
- 페이지
- 8877 ~ 8883