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Nickel-Catalyzed Enantioselective Hydrophosphinylation of 2-Azadienes to Access Enantioenriched α-Aminophosphine Oxides

https://doi.org/10.1021/acscatal.3c02870

Duan, Shengzu; Pan, Ailin; Du, Ya; Zhu, Guanlin; Tian, Xun; Zhang, Hongbin; Walsh, Patrick J; Yang, Xiaodong (August 2023, ACS Catalysis)

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Nickel-catalyzed enantioselective vinylation of aryl 2-azaallyl anions

https://doi.org/10.1039/D1SC00972A

Duan, Shengzu; Deng, Guogang; Zi, Yujin; Wu, Xiaomei; Tian, Xun; Liu, Zhengfen; Li, Minyan; Zhang, Hongbin; Yang, Xiaodong; Walsh, Patrick J. (May 2021, Chemical Science)
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A unique enantioselective nickel-catalyzed vinylation of 2-azaallyl anions is advanced for the first time. This method affords diverse vinyl aryl methyl amines with high enantioselectivities, which are frequently occurring scaffolds in natural products and medications. This C–H functionalization method can also be extended to the synthesis of enantioenriched 1,3-diamine derivatives by employing suitably elaborated vinyl bromides. Key to the success of this process is the identification of a Ni/chiraphos catalyst system and a less reducing 2-azaallyl anion, all of which favor an anionic vinylation route over a background radical reaction. A telescoped gram scale synthesis and a product derivatization study confirmed the scalability and synthetic potential of this method.
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Catalytic Chemo‐ and Regioselective Radical Carbocyanation of 2‐Azadienes for the Synthesis of α‐Amino Nitriles

https://doi.org/10.1002/anie.202300605

Duan, Shengzu; Du, Ya; Wang, Lingling; Tian, Xun; Zi, Yujin; Zhang, Hongbin; Walsh, Patrick J.; Yang, Xiaodong (March 2023, Angewandte Chemie International Edition)

Abstract α‐Amino nitriles are versatile structural motifs in a variety of biologically active compounds and pharmaceuticals and they serve as valuable building blocks in synthesis. The preparation of α‐ and β‐functionalized α‐amino nitriles from readily available scaffolds, however, remains challenging. Herein is reported a novel dual catalytic photoredox/copper‐catalyzed chemo‐ and regioselective radical carbocyanation of 2‐azadienes to access functionalized α‐amino nitriles by using redox‐active esters (RAEs) and trimethylsilyl cyanide. This cascade process employs a broad scope of RAEs and provides the corresponding α‐amino nitrile building blocks in 50–95 % yields (51 examples, regioselectivity >95 : 5). The products were transformed into prized α‐amino nitriles and α‐amino acids. Mechanistic studies suggest a radical cascade coupling process.
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