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铜催化的有机金属试剂与杂环受体的烷基化反应。

Copper-catalysed alkylation of heterocyclic acceptors with organometallic reagents.

作者信息

Guo Yafei, Harutyunyan Syuzanna R

机构信息

Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherlands.

出版信息

Beilstein J Org Chem. 2020 May 14;16:1006-1021. doi: 10.3762/bjoc.16.90. eCollection 2020.

DOI:10.3762/bjoc.16.90
PMID:32509032
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7237809/
Abstract

Copper-catalysed asymmetric C-C bond-forming reactions using organometallic reagents have developed into a powerful tool for the synthesis of complex molecules with single or multiple stereogenic centres over the past decades. Among the various acceptors employed in such reactions, those with a heterocyclic core are of particular importance because of the frequent occurrence of heterocyclic scaffolds in the structures of chiral natural products and bioactive molecules. Hence, this review focuses on the progress made over the past 20 years for heterocyclic acceptors.

摘要

在过去几十年里,使用有机金属试剂的铜催化不对称碳-碳键形成反应已发展成为合成具有单个或多个立体中心的复杂分子的有力工具。在这类反应中使用的各种受体中,具有杂环核心的受体尤为重要,因为在手性天然产物和生物活性分子的结构中经常出现杂环骨架。因此,本综述重点关注过去20年中杂环受体方面取得的进展。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/446f/7237809/4cbecfb040ee/Beilstein_J_Org_Chem-16-1006-g017.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/446f/7237809/cdfb28506952/Beilstein_J_Org_Chem-16-1006-g009.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/446f/7237809/ef610388a052/Beilstein_J_Org_Chem-16-1006-g013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/446f/7237809/239bae575135/Beilstein_J_Org_Chem-16-1006-g014.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/446f/7237809/7e0623a9ba51/Beilstein_J_Org_Chem-16-1006-g015.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/446f/7237809/340e7ba44f5d/Beilstein_J_Org_Chem-16-1006-g016.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/446f/7237809/4cbecfb040ee/Beilstein_J_Org_Chem-16-1006-g017.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/446f/7237809/485df9e28114/Beilstein_J_Org_Chem-16-1006-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/446f/7237809/7b98563fd31e/Beilstein_J_Org_Chem-16-1006-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/446f/7237809/82a1bb60db05/Beilstein_J_Org_Chem-16-1006-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/446f/7237809/68548d2650db/Beilstein_J_Org_Chem-16-1006-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/446f/7237809/dd969605b71d/Beilstein_J_Org_Chem-16-1006-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/446f/7237809/2139aa5b373b/Beilstein_J_Org_Chem-16-1006-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/446f/7237809/e0bf37fbaf7b/Beilstein_J_Org_Chem-16-1006-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/446f/7237809/cdfb28506952/Beilstein_J_Org_Chem-16-1006-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/446f/7237809/39ef6b2177af/Beilstein_J_Org_Chem-16-1006-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/446f/7237809/a7068d31e410/Beilstein_J_Org_Chem-16-1006-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/446f/7237809/d3450543d63b/Beilstein_J_Org_Chem-16-1006-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/446f/7237809/ef610388a052/Beilstein_J_Org_Chem-16-1006-g013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/446f/7237809/239bae575135/Beilstein_J_Org_Chem-16-1006-g014.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/446f/7237809/7e0623a9ba51/Beilstein_J_Org_Chem-16-1006-g015.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/446f/7237809/340e7ba44f5d/Beilstein_J_Org_Chem-16-1006-g016.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/446f/7237809/4cbecfb040ee/Beilstein_J_Org_Chem-16-1006-g017.jpg

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1
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Angew Chem Int Ed Engl. 2019 Sep 9;58(37):12950-12954. doi: 10.1002/anie.201906237. Epub 2019 Jul 30.
2
Recent advances in the asymmetric synthesis of pharmacology-relevant nitrogen heterocycles via stereoselective aza-Michael reactions.通过立体选择性氮杂迈克尔反应实现药理学相关氮杂环的不对称合成的最新进展。
Org Biomol Chem. 2019 Apr 10;17(15):3670-3708. doi: 10.1039/c8ob03034k.
3
Desymmetrization of meso-bisphosphates using copper catalysis and alkylzirconocene nucleophiles.
钌催化乙烯基吡啶与醛/酮的β-选择性烷基化反应及NH介导的脱氧偶联反应。
Chem Sci. 2020 Dec 30;12(8):2870-2875. doi: 10.1039/d0sc06586b.
使用铜催化和烷基锆烯亲核试剂对介-双膦酸盐进行去对称化。
Nat Commun. 2019 Jan 3;10(1):21. doi: 10.1038/s41467-018-07871-x.
4
β-Chloroaldehydes from Trapping Zirconium Enolates Produced in Asymmetric 1,4-Additions.
Org Lett. 2019 Jan 18;21(2):378-381. doi: 10.1021/acs.orglett.8b03520. Epub 2018 Dec 31.
5
Highly enantioselective catalytic synthesis of chiral pyridines.高对映选择性催化合成手性吡啶。
Nat Commun. 2017 Dec 12;8(1):2058. doi: 10.1038/s41467-017-01966-7.
6
Asymmetric cross-coupling of alkyl, alkenyl and (hetero)aryl nucleophiles with racemic allyl halides.烷基、烯基和(杂)芳基亲核试剂与外消旋烯丙基卤化物的不对称交叉偶联反应。
Chem Commun (Camb). 2017 Nov 21;53(93):12499-12511. doi: 10.1039/c7cc07151e.
7
Lewis Acid Enabled Copper-Catalyzed Asymmetric Synthesis of Chiral β-Substituted Amides.路易斯酸促进的铜催化手性β-取代酰胺的不对称合成。
J Am Chem Soc. 2017 Oct 11;139(40):14224-14231. doi: 10.1021/jacs.7b07344. Epub 2017 Sep 29.
8
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Chem Sci. 2017 Jan 1;8(1):641-646. doi: 10.1039/c6sc02811j. Epub 2016 Sep 2.
9
Mechanistic Studies on a Cu-Catalyzed Asymmetric Allylic Alkylation with Cyclic Racemic Starting Materials.手性环状外消旋起始原料的铜催化不对称烯丙基烷基化反应的机理研究。
J Am Chem Soc. 2017 Apr 19;139(15):5614-5624. doi: 10.1021/jacs.7b02440. Epub 2017 Apr 10.
10
Catalytic asymmetric addition of Grignard reagents to alkenyl-substituted aromatic N-heterocycles.手性催化格氏试剂对烯基取代芳基氮杂环的不对称加成反应。
Science. 2016 Apr 22;352(6284):433-7. doi: 10.1126/science.aaf1983.