CpRh 促进的不对称烯基 C-H 官能化反应通过丙烯酰胺和烯丙基的 [4+1]-环加成反应形成 2H-吡咯-2-酮。
Asymmetric Alkenyl C-H Functionalization by Cp Rh forms 2H-Pyrrol-2-ones through [4+1]-Annulation of Acryl Amides and Allenes.
机构信息
Laboratory of Asymmetric Catalysis and Synthesis, EPFL SB ISIC LCSA, BCH 4305, CH-1015, Lausanne, Switzerland.
Dipartimento di Chimica, Università di Bologna, via Selmi 2, 40126, Bologna, Italy.
出版信息
Angew Chem Int Ed Engl. 2019 Dec 9;58(50):18136-18140. doi: 10.1002/anie.201909971. Epub 2019 Oct 28.
An efficient Cp Rh -catalyzed enantioselective alkenyl C-H functionalization/[4+1] annulation of acryl amides and allenes is reported. The described transformation provides straightforward access to enantioenriched α,β-unsaturated-γ-lactams bearing a quaternary stereocenter. The reaction operates under mild conditions, displays a broad functional-group tolerance, and provides 2H-pyrrol-2-ones with excellent selectivity of up to 97:3 er. Such scaffolds are frequently found in natural products and synthetic bioactive compounds and are of significant synthetic value. It is noteworthy that the allene serves as a one-carbon unit in the [4+1]-annulation.
报道了一种高效的 CpRh 催化的对映选择性烯基 C-H 官能化/[4+1]环加成反应，用于丙烯酰胺和丙二烯的反应。所描述的转化提供了直接获得手性富集的α,β-不饱和-γ-内酰胺的方法，其中含有一个季立体中心。该反应在温和的条件下进行，具有广泛的官能团容忍性，并提供了具有高达 97:3 er 的优异选择性的 2H-吡咯-2-酮。这些支架经常存在于天然产物和合成生物活性化合物中，具有重要的合成价值。值得注意的是，丙二烯在[4+1]-环加成反应中充当一碳单元。
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