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不对称有机催化向硝基烯烃的共轭加成反应的最新进展

Recent Advances in Asymmetric Organocatalyzed Conjugate Additions to Nitroalkenes.

作者信息

Alonso Diego A, Baeza Alejandro, Chinchilla Rafael, Gómez Cecilia, Guillena Gabriela, Pastor Isidro M, Ramón Diego J

机构信息

Department of Organic Chemistry and Institute of Organic Synthesis (ISO), Faculty of Sciences, University of Alicante, PO Box 99, 03080 Alicante, Spain.

出版信息

Molecules. 2017 May 29;22(6):895. doi: 10.3390/molecules22060895.

DOI:10.3390/molecules22060895
PMID:28555049
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6152790/
Abstract

The asymmetric conjugate addition of carbon and heteroatom nucleophiles to nitroalkenes is a very interesting tool for the construction of highly functionalized synthetic building blocks. Thanks to the rapid development of asymmetric organocatalysis, significant progress has been made during the last years in achieving efficiently this process, concerning chiral organocatalysts, substrates and reaction conditions. This review surveys the advances in asymmetric organocatalytic conjugate addition reactions to α,β-unsaturated nitroalkenes developed between 2013 and early 2017.

摘要

碳和杂原子亲核试剂对硝基烯烃的不对称共轭加成是构建高度官能化合成砌块的一种非常有趣的方法。由于不对称有机催化的迅速发展,在过去几年中,在手性有机催化剂、底物和反应条件方面,实现这一过程已取得了重大进展。本文综述了2013年至2017年初开发的α,β-不饱和硝基烯烃不对称有机催化共轭加成反应的研究进展。

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Molecules. 2024 Jan 22;29(2):542. doi: 10.3390/molecules29020542.
5
Crystallization-Enabled Stereoconvergent Michael Additions of β-Keto Esters to Nitroolefins.β-酮酯与硝基烯烃的结晶促进立体汇聚迈克尔加成反应
Org Lett. 2023 Sep 15;25(36):6779-6783. doi: 10.1021/acs.orglett.3c02799. Epub 2023 Sep 5.
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Accessing Chiral Pyrrolodiketopiperazines under Organocatalytic Conditions.手性吡咯并二酮哌嗪的有机催化合成条件。
Org Lett. 2023 Jan 13;25(1):125-129. doi: 10.1021/acs.orglett.2c03924. Epub 2022 Dec 29.
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Stereoselective Synthesis of Spiro-Decalin Oxindole Derivatives via Sequential Organocatalytic Michael-Domino Michael/Aldol Reaction.通过顺序有机催化迈克尔-多米诺迈克尔/Aldol 反应立体选择性合成螺-十氢吲哚酮衍生物。
J Org Chem. 2022 Aug 5;87(15):10454-10461. doi: 10.1021/acs.joc.2c01046. Epub 2022 Jul 25.
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Asymmetric Michael Addition in Synthesis of β-Substituted GABA Derivatives.不对称迈克尔加成在β-取代 GABA 衍生物合成中的应用。
Molecules. 2022 Jun 13;27(12):3797. doi: 10.3390/molecules27123797.
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Silica gel-immobilized multidisciplinary materials applicable in stereoselective organocatalysis and HPLC separation.适用于立体选择性有机催化和高效液相色谱分离的硅胶固定化多学科材料。
RSC Adv. 2018 Jan 3;8(3):1174-1181. doi: 10.1039/c7ra12658a. eCollection 2018 Jan 2.
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Copper-free Sonogashira cross-coupling reactions: an overview.无铜的Sonogashira交叉偶联反应:综述
RSC Adv. 2021 Feb 10;11(12):6885-6925. doi: 10.1039/d0ra10575a. eCollection 2021 Feb 4.
水相促进的惰性硝基烯烃的不对称迈克尔反应:一锅法合成具有全碳季碳手性中心的手性 GABA 类似物。
Angew Chem Int Ed Engl. 2017 Feb 6;56(7):1835-1839. doi: 10.1002/anie.201611466. Epub 2017 Jan 18.
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Bifunctional Brønsted Base Catalyst Enables Regio-, Diastereo-, and Enantioselective C -Alkylation of β-Tetralones and Related Aromatic-Ring-Fused Cycloalkanones.双功能布朗斯特碱催化剂实现β-四氢萘酮及相关稠合芳环环烷酮的区域、非对映选择性和对映选择性 C-烷基化。
Angew Chem Int Ed Engl. 2017 Feb 13;56(8):2059-2063. doi: 10.1002/anie.201612332. Epub 2017 Jan 18.
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Asymmetric Synthesis of Rauhut-Currier type Products by a Regioselective Mukaiyama Reaction under Bifunctional Catalysis.双功能催化下通过区域选择性 Mukaiyama 反应对 Rauhut-Currier 型产物的不对称合成。
J Am Chem Soc. 2017 Jan 18;139(2):672-679. doi: 10.1021/jacs.6b07851. Epub 2017 Jan 9.
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Stereoselective Synthesis of α-Fluoro-γ-nitro Thioesters under Organocatalytic Conditions.手性催化条件下α-氟-γ-硝基硫代酯的立体选择性合成。
Org Lett. 2016 Dec 2;18(23):6014-6017. doi: 10.1021/acs.orglett.6b02795. Epub 2016 Nov 11.
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Highly enantioselective Michael addition of cyclohexanone to nitroolefins catalyzed by pyrrolidine-based bifunctional benzoylthiourea in water.基于吡咯烷的双功能苯甲酰硫脲在水中催化环己酮与硝基烯烃的高对映选择性迈克尔加成反应。
Chirality. 2016 Nov;28(11):721-727. doi: 10.1002/chir.22648.
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Catalytic Asymmetric Conjugate Addition and Sulfenylation of Diarylthiazolidin-2,4-diones.二芳基噻唑烷-2,4-二酮的催化不对称共轭加成和亚磺酰化反应。
J Org Chem. 2016 Oct 21;81(20):9620-9629. doi: 10.1021/acs.joc.6b01637. Epub 2016 Sep 30.
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Therapeutic Potential of Spirooxindoles as Antiviral Agents.螺环氧化吲哚作为抗病毒药物的治疗潜力
ACS Infect Dis. 2016 Jun 10;2(6):382-92. doi: 10.1021/acsinfecdis.6b00041. Epub 2016 May 5.
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Oxindole: A chemical prism carrying plethora of therapeutic benefits.氧化吲哚:一个承载着丰富治疗益处的化学棱镜。
Eur J Med Chem. 2016 Nov 10;123:858-894. doi: 10.1016/j.ejmech.2016.08.011. Epub 2016 Aug 8.