氮丙啶
立体中心
亚甲基
化学
氮杂环丁烷
立体选择性
立体化学
戒指(化学)
双环分子
药物化学
对映选择合成
有机化学
催化作用
作者
Steven C. Schmid,Ilia A. Guzei,Jennifer M. Schomaker
标识
DOI:10.1002/anie.201705202
摘要
Abstract The reaction of rhodium‐bound carbenes with strained bicyclic methylene aziridines results in a formal [3+1] ring expansion to yield highly substituted methylene azetidines with excellent regio‐ and stereoselectivity. The reaction appears to proceed through an ylide‐type mechanism, where the unique strain and structure of the methylene aziridine promotes a ring‐opening/ring‐closing cascade that efficiently transfers chirality from substrate to product. The resultant products can be elaborated into new azetidine scaffolds containing vicinal tertiary‐quaternary and even quaternary‐quaternary stereocenters.
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