期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 55, 期 6, 页码 2222-2225出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201510152
关键词
carbenes; C-C cleavage; 1; 3-dipolar cycloaddition; pyrazoles; unsaturated ketones
资金
- UIC (LAS Science Award)
- NSF [CHE 0955972]
- Petroleum Research Fund
,-Unsaturated ketones generally undergo addition reactions with nucleophiles with a preference for either 1,2- or 1,4-addition, but rarely both. However, the right combination of reagents allows for consecutive 1,4- and 1,2-additions to occur: Cyclic ,-unsaturated ketones undergo double additions with lithium(trimethylsilyl)diazomethane, effectively generating various molecular frameworks with complexity and diversity. Owing to the sequential generation of several intermediates of multifaceted reactivity, including diazoalkane derivatives and alkylidene carbenes, it is possible to induce novel Grob-type C-C fragmentations, alkylidene carbene mediated Li-N insertions, and dipolar cycloadditions by controlling the reaction parameters.
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