1. Catalytic [3 + 2] Cycloaddition through Ring Cleavage of Simple Cyclopropanes with Isocyanates
- Author
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Itaru Suzuki, Ikuya Shibata, Yoshiaki Maruoka, and Shinji Tsunoi
- Subjects
Bromides ,Cyclopropanes ,Lactams ,Iodide ,Magnesium Compounds ,chemistry.chemical_element ,Ate complex ,Ring (chemistry) ,Biochemistry ,Medicinal chemistry ,Catalysis ,chemistry.chemical_compound ,Nucleophile ,Organic chemistry ,Physical and Theoretical Chemistry ,chemistry.chemical_classification ,Cycloaddition Reaction ,Molecular Structure ,Aryl ,Organic Chemistry ,Stereoisomerism ,Cycloaddition ,chemistry ,Cyclization ,Tin ,Isocyanates - Abstract
The catalytic synthesis of γ-butyrolactams was established via [3 + 2]-cycloaddition of cyclopropanes with isocyanates. An organotin iodide ate complex, MgBr(+)[Bu2SnBrI2](-), was employed as an effective catalyst. Simple cyclopropanes that lack aryl or vinyl substituents were useful precursors. Even acyl cyclopropanes were applicable. The hybrid characteristics of a tin complex, acidic MgBr(+) with nucleophilic tin iodide, was responsible for the catalytic reaction.
- Published
- 2015
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