Microwave- and photoirradiation-induced staudinger reactions of cyclic imines and ketenes generated from alpha-diazoketones. A further investigation into the stereochemical process |
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| Authors: | Liang Yong Jiao Lei Zhang Shiwei Xu Jiaxi |
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| Institution: | Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Department of Chemical Biology, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, P. R. China. |
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| Abstract: | Reactions of ketenes generated from alpha-diazoketones with a series of acyclic and cyclic imines were investigated under both microwave and photoirradiation conditions. The results indicate that the zwitterionic azabutadiene-type intermediates yielded from imines and ketenes undergo a conrotatory ring closure exclusively to produce beta-lactams. It is notable that no Woodward-Hoffmann product was found under the ultraviolet irradiation. The photoirradiation-induced Staudinger reaction shows a different stereoselectivity from the electrocyclic reaction of substituted 1,3-butadiene. |
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