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手性 N-N 轴联 1,1'-联吡啶的对映选择性合成:手性磷酸催化与路易斯酸诱导的对映体发散。

Atroposelective Synthesis of 1,1'-Bipyrroles Bearing a Chiral N-N Axis: Chiral Phosphoric Acid Catalysis with Lewis Acid Induced Enantiodivergence.

机构信息

Joint School of National University of Singapore and Tianjin University, International Campus of Tianjin University, Binhai New City, Fuzhou, 350207, China.

Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore, 117543, Republic of Singapore.

出版信息

Angew Chem Int Ed Engl. 2022 Apr 11;61(16):e202200371. doi: 10.1002/anie.202200371. Epub 2022 Feb 24.

DOI:10.1002/anie.202200371
PMID:35174596
Abstract

We present herein a highly efficient atroposelective synthesis of axially chiral 1,1'-bipyrroles bearing an N-N linkage from simple hydrazine and 1,4-diones. Further product derivatizations led to axially chiral bifunctional compounds with high potential in asymmetric catalysis. For this chrial phosphoric acid (CPA)-catalyzed double Paal-Knorr reaction, an intriguing Fe(OTf) -induced enantiodivergence was also observed.

摘要

我们在此展示了一种高效的轴手性 1,1'-联吡啶的对映选择性合成方法,该方法使用简单的肼和 1,4-二酮作为原料。进一步的产物衍生化得到了具有高潜力的轴手性双官能化合物,在不对称催化中有很好的应用。在这种手性磷酸(CPA)催化的双 Paal-Knorr 反应中,还观察到了一种有趣的 Fe(OTf)诱导的对映体发散现象。

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