Cycloadditions of N-sulfonyl nitrones generated by lewis acid catalyzed rearrangement of oxaziridines
Cycloadditions of N-sulfonyl nitrones generated by lewis acid catalyzed rearrangement of oxaziridines
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DOI：
10.1021/ja711335d
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发表时间：
2008-03-12
影响因子：
15
通讯作者：
Yoon, Tehshik P.
中科院分区：
文献类型：
--
作者：
Partridge, Katherine M.;Anzovino, Mary E.;Yoon, Tehshik P.
我们已经开发了新的，缺电子的N-nosyl硝酮，产生从钛（IV）催化重排相应的N-nosyl oxaziridines的环加成反应。各种各样的苯乙烯和氧氮杂环丙烷在这种转化中顺利地反应，以良好的产率和优异的非对映选择性产生结构不同的N-硝基苯磺酰基异恶唑烷。重要的是，可以在温和条件下容易地去除nosyl保护基团，而不会伴随敏感的异恶唑烷氮-氧键的断裂，从而允许有效地获得N-未取代的异恶唑烷用于进一步的合成操作和生物学评价。
We have developed cycloaddition reactions of novel, electron-deficient N-nosyl nitrones that arise from the titanium(IV)-catalyzed rearrangement of the corresponding N-nosyl oxaziridines. A diverse range of styrenes and oxaziridines react smoothly in this transformation, producing structurally varied N-nosyl isoxazolidines in good yields and with excellent diastereoselectivity. Importantly, the nosyl protecting group can be easily removed under mild conditions without concomitant cleavage of the sensitive isoxazolidine nitrogen-oxygen bond, allowing efficient access to N-unsubstituted isoxazolidines for further synthetic manipulation and biological evaluation.