A potentially general method to control relative stereochemistry in enone–olefin 2+2-photocycloaddition reactions by using eniminium salt surrogates
作者:Xiaolu Cai、Virginia Chang、Chuanfeng Chen、Hyun-Jin Kim、Patrick S Mariano
DOI:10.1016/s0040-4039(00)01581-1
日期:2000.12
A new strategy to control the stereochemistry of enone–olefin 2+2-photocycloaddition reactions, based on the use of eniminium salt surrogates, is experimentally tested. In contrast to enone–olefin photocycloadditions, which emanate from enone triplet excited states and follow non-concerted pathways, analogous reactions of conjugated eniminium salts can occur by singlet, concerted routes and, as a result
通过使用tested胺盐替代物来控制烯-烯烃2 + 2-光环加成反应的立体化学的新策略已通过实验测试。与烯酮-烯烃光环加成反应(源自烯酮三重态激发态并遵循未证实的途径)相反,共轭亚胺盐的类似反应可通过单峰,一致的途径发生,因此,可完全控制含有环丁烷环的产物相对立体化学 通过使用一系列的imi盐测试了该建议,这些imi盐包含富电子和贫电子的烯烃系链。结果表明,这些底物的分子内2 + 2-光环加成显示中等至高度的立体特异性。