Diastereoselective Allylation of Aldehydes by Dual Photoredox and Chromium Catalysis,Journal of the American Chemical Society

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Diastereoselective Allylation of Aldehydes by Dual Photoredox and Chromium Catalysis
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2018-09-14 , DOI: 10.1021/jacs.8b08052
J. Luca Schwarz ₁ , Felix Schäfers ₁ , Adrian Tlahuext-Aca ₁ , Lukas Lückemeier ₁ , Frank Glorius ₁

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Herein, we report the redox-neutral allylation of aldehydes with readily available electron-rich allyl (hetero-) arenes, β-alkyl styrenes and allyl-diarylamines. This process was enabled by the combination of photoredox and chromium catalysis, which allowed a range of homoallylic alcohols to be prepared with high levels of selectivity for the anti diastereomer. Mechanistic investigations support the formation of an allyl chromium intermediate from allylic C(sp3)-H bonds and thus significantly extends the scope of the venerable Nozaki-Hiyama-Kishi reaction.

中文翻译：

双光氧化还原和铬催化非对映选择性烯丙基化醛

在此，我们报告了醛与容易获得的富电子烯丙基（杂）芳烃、β-烷基苯乙烯和烯丙基二芳基胺的氧化还原中性烯丙基化。该过程是通过光氧化还原和铬催化的组合实现的，这使得一系列高烯丙醇能够以高水平的抗非对映异构体选择性制备。机理研究支持从烯丙基 C(sp3)-H 键形成烯丙基铬中间体，从而显着扩展了古老的 Nozaki-Hiyama-Kishi 反应的范围。

更新日期：2018-09-14

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