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季铵盐催化异恶唑烷-5-酮对烯丙酸酯的对映选择性β-选择性加成反应

Enantioselective β-Selective Addition of Isoxazolidin-5-ones to Allenoates Catalyzed by Quaternary Ammonium Salts.

作者信息

Zebrowski Paul, Röser Katharina, Chrenko Daniel, Pospíšil Jiří, Waser Mario

机构信息

Institute of Organic Chemistry, Johannes Kepler University Linz, Altenbergerstrasse 69, 4040 Linz, Austria.

Department of Chemical Biology, Faculty of Science, Palacký University, Šlechtitelů 27, 783 71 Olomouc, Czech Republic.

出版信息

Synthesis (Stuttg). 2023 Jun;55(11):1706-1713. doi: 10.1055/a-1948-5493. Epub 2022 Oct 27.

DOI:10.1055/a-1948-5493
PMID:38855403
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7616069/
Abstract

The enantioselective addition of isoxazolidin-5-ones to the β-carbon of allenoates has been carried out by using a novel spirobiindane-based quaternary ammonium salt catalyst. This protocol, which proceeds under classical liquid-solid phase-transfer conditions, gives access to unprecedented highly functionalized β-amino acid derivatives with good enantioselectivities and in high yields, and further manipulations of these products have been carried out as well.

摘要

通过使用一种新型的基于螺双茚满的季铵盐催化剂，实现了异恶唑烷-5-酮对烯丙酸酯β-碳的对映选择性加成。该方法在经典的液-固相转移条件下进行，能够得到前所未有的高官能化β-氨基酸衍生物，对映选择性良好且产率高，并且对这些产物也进行了进一步的操作。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1610/7616069/0ad01771baeb/EMS196536-f006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1610/7616069/245154451b6d/EMS196536-f007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1610/7616069/2fe5e872f53c/EMS196536-f001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1610/7616069/c363dd91a16d/EMS196536-f002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1610/7616069/7303b910922f/EMS196536-f003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1610/7616069/f068fdad6bd8/EMS196536-f004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1610/7616069/6d0d4d0b6ef6/EMS196536-f005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1610/7616069/0ad01771baeb/EMS196536-f006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1610/7616069/245154451b6d/EMS196536-f007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1610/7616069/2fe5e872f53c/EMS196536-f001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1610/7616069/c363dd91a16d/EMS196536-f002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1610/7616069/7303b910922f/EMS196536-f003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1610/7616069/f068fdad6bd8/EMS196536-f004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1610/7616069/6d0d4d0b6ef6/EMS196536-f005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1610/7616069/0ad01771baeb/EMS196536-f006.jpg

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本文引用的文献

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J Org Chem. 2022 Jul 1;87(13):8730-8743. doi: 10.1021/acs.joc.2c01034. Epub 2022 Jun 22.
2
Reactivities of allenic and olefinic Michael acceptors towards phosphines.联烯型和烯型迈克尔受体对膦的反应活性。
Chem Commun (Camb). 2022 Mar 8;58(20):3358-3361. doi: 10.1039/d1cc06786a.
3
Enantioselective Catalytic Synthesis of α-Halogenated α-Aryl-β-amino Acid Derivatives.
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4
Enantioselective organocatalytic syntheses of α-selenated α- and β-amino acid derivatives.对映选择性有机催化合成α-硒代α-和β-氨基酸衍生物。
Org Biomol Chem. 2022 Jan 26;20(4):824-830. doi: 10.1039/d1ob02235k.
5
Imbuing an Old Heterocycle with the Power of Modern Catalysis: An Isoxazolidin-5-one Story.赋予古老杂环以现代催化的力量：异噁唑烷-5-酮的故事。
Chem Pharm Bull (Tokyo). 2021;69(12):1160-1169. doi: 10.1248/cpb.c21-00750.
6
Development of -Symmetric Chiral Spirocyclic Phase-Transfer Catalysts: Synthesis and Application to Asymmetric Alkylation of Glycinate Schiff Base.不对称手性螺环相转移催化剂的开发：甘氨酸席夫碱不对称烷基化反应中的合成与应用
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7
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Angew Chem Int Ed Engl. 2020 Dec 21;59(52):23516-23520. doi: 10.1002/anie.202009892. Epub 2020 Oct 19.
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