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Dealkenylative Alkenylation: Formal σ-Bond Metathesis of Olefins.
Angewandte Chemie International Edition ( IF 16.6 ) Pub Date : 2020-07-11 , DOI: 10.1002/anie.202005267
Manisha Swain 1 , Gusein Sadykhov 1 , Ruoxi Wang 1 , Ohyun Kwon 1
Affiliation  

The dealkenylative alkenylation of alkene C(sp3)−C(sp2) bonds has been an unexplored area for C−C bond formation. Herein 64 examples of β‐alkylated styrene derivatives, synthesized through the reactions of readily accessible feedstock olefins with β‐nitrostyrenes by ozone/FeII‐mediated radical substitutions, are reported. These reactions proceed with good efficiencies and high stereoselectivities under mild reaction conditions and tolerate an array of functional groups. Also demonstrated is the applicability of the strategy through several synthetic transformations of the products, as well as the syntheses of the natural product iso‐moracin and the drug (E)‐metanicotine.

中文翻译:

脱烯基烯化:烯烃的形式σ键复分解。

烯烃C(sp 3)-C(sp 2)键的脱烯基烯基化作用一直是C-C键形成的未知区域。本文报道了64个β-烷基化苯乙烯衍生物的例子,这些例子是通过容易获得的原料烯烃与β-硝基苯乙烯通过臭氧/ Fe II介导的自由基取代反应而合成的。在温和的反应条件下,这些反应具有良好的效率和较高的立体选择性,并且可以耐受一系列官能团。还证明了该策略通过产品的几种合成转化以及天然产物异吗啡丁和药物(E)-美丹尼丁的合成的适用性。
更新日期:2020-07-11
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