Ring Expansion, Ring Contraction, and Annulation Reactions of Allylic Phosphonates under Oxidative Cleavage Conditions
Ring Expansion, Ring Contraction, and Annulation Reactions of Allylic Phosphonates under Oxidative Cleavage Conditions
复制标题
氧化裂解条件下烯丙基膦酸酯的扩环、缩环和成环反应
DOI：
10.1021/acs.orglett.8b00791
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发表时间：
2018
期刊：
影响因子：
5.2
通讯作者：
Minehan, Thomas G.
中科院分区：
文献类型：
--
作者：
Orr, Dupre;Yousefi, Nikolas;Minehan, Thomas G.
氧化裂解环烯基烷基膦酸盐1，然后用碱处理，得到收率高至优异的同源环烯酮2。在相同的条件下制备2-烯基膦酸环，可以得到收率很高的单碳环缩化合物。γ，δ-不饱和酮膦酸盐6的氧化裂解，然后用碱处理，可以得到2-环戊烯-1-酮膦7，总的产率很高。该方法可为实现单碳环膨胀、环收缩和成环反应提供一种实用的替代方法。
Oxidative cleavage of cycloalkenylalkylphosphonates1followed by treatment with base gives rise to homologated cycloalkenones2in good to excellent yields. Subjecting cycloalk-2-enylphosphonates3to identical conditions provides the one-carbon ring-contracted compounds4in excellent yields. Oxidative cleavage of γ,δ-unsaturated ketophosphonates6followed by treatment with base affords 2-cyclopenten-1-ones7in good overall yields. This method may offer a practical alternative to existing methods for effecting one-carbon ring expansion, ring contraction, and annulation reactions.