flow_chemi​stry

Application of Transition-Metal Catalysis, Biocatalysis, and Flow Chemistry as State-of-the-Art Technologies in the Synthesis of LCZ696

http://feedproxy.google.com/~r/acs/joceah/~3/q0Gm3XBDMkE/acs.joc.0c00473

TOC Graphic

The Journal of Organic Chemistry
DOI: 10.1021/acs.joc.0c00473

Authors: Xingxian Gu†, Jibin Zhao†, Like Chen†, Yunzhong Li†, Bo Yu†, Xiangguang Tian†, Zhongcheng Min†, Su Xu†, Huijuan Gu†, Junjie Sun†, Xiaoquan Lu†, Meng Chang†, Xufan Wang†, Liqun Zhao†, Shengqing Ye†, Hongwei Yang†, Yingtao Tian†, Feng Gao†, Yu Gai†, Guanghua Jia‡, Jingjing Wu‡, Yan Wang‡, Jianghua Zhang‡, Xuesong Zhang‡, Weichun Liu‡, Xin Gu‡, Xi Luo‡, Hai Dong‡, Huaimin Wang‡, Berthold Schenkel§, Francesco Venturoni§, Paolo Filipponi§, Bertrand Guelat§, Thomas Allmendinger§, Bernhard Wietfeld§, Pascale Hoehn§, Nikola Kovacic§, Luca Hermann§, Thierry Schlama§, Thomas Ruch§, Nadine Derrien?, Philippe Piechon?, and Florian Kleinbeck*§

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Continuous-Flow Synthesis of (–)-Oseltamivir Phosphate (Tamiflu)

SynlettDOI: 10.1055/s-0039-1690878Herein the anti-influenza drug (–)-oseltamivir phosphate is prepared in continuous flow from ethyl shikimate with 54% overall yield over nine steps and total residence time of 3.5 min from the individual steps. Although the procedure involved intermediate isolation, the dangerous azide chemistry and intermediates involved were elegantly handled in situ. It is the first continuous-flow process for (–)-oseltamivir phosphate involving azide chemistry and (–)-shikimic acid as precursor.[…]© Georg Thieme Verlag Stuttgart · New YorkArticle in Thieme eJournals:Table of contents  |  Abstract  |  Full text

Authors: Sagandira, Cloudius R.http://dx.doi.org/10.1055/s-0039-1690878

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Recent Advances in Continuous‐Flow Enantioselective Catalysis

Going with the flow: In recent years, continuous‐flow techniques have received considerable attention and shown rapid progress in manufacturing. Among these, catalytic enantioselective flow processes using homogeneous, heterogeneous, or enzymatic catalysts have shown significant advantages over the conventional batch mode. In this Minireview, recent advances in continuous‐flow enantioselective catalysis are summarized and discussed, with emphasis on studies published after 2013.AbstractThe increased demand for more efficient, safe, and green production in fine chemical and pharmaceutical industry calls for the development of continuous‐flow manufacturing, and for chiral chemicals in particular, enantioselective catalytic processes. In recent years, this emerging direction has received considerable attention and has seen rapid progress. In most cases, catalytic enantioselective flow processes using homogeneous, heterogeneous, or enzymatic catalysts have shown significant advantages over the conventional batch mode, such as shortened reaction times, lower catalysts loadings, and higher selectivities in addition to the normal merits of non‐enantioselective flow operations. In this Minireview, the advancements, key strategies, methods, and technologies developed the last six years as well as remaining challenges are summarized.

Authors: Tao Yu, Zhengwei Ding, Wenzheng Nie, Jiao Jiao, Hailong Zhang, Qian Zhang, Chao Xue, Xinhua Duan, Yoichi M. A. Yamada, Pengfei Lihttps://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/chem.201905151?af=R

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Continuous Flow Organophosphorus Chemistry

Organophosphorus derivatives are widespread compounds that chemists find from the bench to the plant, with numerous daily life applications. Besides their common utility for a wide range of notorious reactions such as the Wittig and HWE olefinations, the Arbuzov reaction, the Staudinger reaction, the Mitsunobu reaction as well as ligands for a large variety of organometallic complexes, organophosphorus compounds have also found numerous applications as active pharmaceutical ingredients and agrochemicals. Some organophosphorus derivatives are also infamously known as Chemical Warfare Agents. Within the context of generalized adoption of new process technologies in the Chemistry Toolbox, this review intends to give an update on the most recent and significant advances in continuous flow organophosphorus chemistry. Selected examples in methodology, total synthesis and for the preparation of industrially relevant targets are discussed for illustrating the assets of flow chemistry.Authors: Romain Morodo, Pauline Bianchi, Jean-Christophe M. Monbaliuhttps://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.202000430?af=R

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Continuous Flow Enables Metallaphotoredox Catalysis in a Medicinal Chemistry Setting: Accelerated Optimization and Library Execution of a Reductive Coupling between Benzylic Chlorides and Aryl Bromides

Merck
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  • Z.G. Brill, C.B. Ritts, U.F. Mansoor, and N. Sciammetta, "Continuous Flow Enables Metallaphotoredox Catalysis in a Medicinal Chemistry Setting: Accelerated Optimization and Library Execution of a Reductive Coupling between Benzylic Chlorides and Aryl Bromides", Organic Letters, vol. 22, pp. 410-416, 2019. http://dx.doi.org/10.1021/acs.orglett.9b04117
  • A robotic platform for flow synthesis of organic compounds informed by AI planning

    [new paper by Timothy F. Jamison and Klavs F. Jensen]

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  • C.W. Coley, D.A. Thomas, J.A.M. Lummiss, J.N. Jaworski, C.P. Breen, V. Schultz, T. Hart, J.S. Fishman, L. Rogers, H. Gao, R.W. Hicklin, P.P. Plehiers, J. Byington, J.S. Piotti, W.H. Green, A.J. Hart, T.F. Jamison, and K.F. Jensen, "A robotic platform for flow synthesis of organic compounds informed by AI planning", Science, vol. 365, pp. eaax1566, 2019. http://dx.doi.org/10.1126/science.aax1566
  • Visible‐Light‐Promoted Iron‐Catalyzed C(sp2)–C(sp3) Kumada Cross‐Coupling in Flow

    [Timothy Noel]

    [1]

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  • X. Wei, I. Abdiaj, C. Sambiagio, C. Li, E. Zysman‐Colman, J. Alcázar, and T. Noël, "Visible‐Light‐Promoted Iron‐Catalyzed C(sp 2 )–C(sp 3 ) Kumada Cross‐Coupling in Flow", Angewandte Chemie International Edition, vol. 58, pp. 13030-13034, 2019. http://dx.doi.org/10.1002/anie.201906462
  • Development of a Continuous Flow Process for a Matteson Reaction: From Lab Scale to Full-Scale Production of a Pharmaceutical Intermediate


    [1]

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  • C. Stueckler, P. Hermsen, B. Ritzen, M. Vasiloiu, P. Poechlauer, S. Steinhofer, A. Pelz, C. Zinganell, U. Felfer, S. Boyer, M. Goldbach, A. de Vries, T. Pabst, G. Winkler, V. LaVopa, S. Hecker, and C. Schuster, "Development of a Continuous Flow Process for a Matteson Reaction: From Lab Scale to Full-Scale Production of a Pharmaceutical Intermediate", Organic Process Research & Development, vol. 23, pp. 1069-1077, 2019. http://dx.doi.org/10.1021/acs.oprd.8b00340
  • Acoustic Droplet Ejection Enabled Automated Reaction Scouting

    [Dömling lab with Astra-Zeneca]

    [1]

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  • Y. Wang, S. Shaabani, M. Ahmadianmoghaddam, L. Gao, R. Xu, K. Kurpiewska, J. Kalinowska-Tluscik, J. Olechno, R. Ellson, M. Kossenjans, V. Helan, M. Groves, and A. Dömling, "Acoustic Droplet Ejection Enabled Automated Reaction Scouting", ACS Central Science, vol. 5, pp. 451-457, 2019. http://dx.doi.org/10.1021/acscentsci.8b00782