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手性氮杂环丙烷功能化有机磷化合物促进的高效不对称[3+2]环加成反应

Highly Efficient Asymmetric [3+2] Cycloaddition Promoted by Chiral Aziridine-Functionalized Organophosphorus Compounds.

作者信息

Szymańska Julia, Rachwalski Michał, Pieczonka Adam M

机构信息

Department of Organic and Applied Chemistry, Faculty of Chemistry, University of Lodz, Tamka 12, PL-91-403 Lodz, Poland.

Doctoral School of Exact and Natural Sciences, University of Lodz, Matejki 21/23, PL-90-237 Lodz, Poland.

出版信息

Molecules. 2024 Jul 11;29(14):3283. doi: 10.3390/molecules29143283.

DOI:10.3390/molecules29143283
PMID:39064862
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11279481/
Abstract

The asymmetric [3+2] cycloaddition of azomethine ylides generated from the corresponding imino ester-to--β-nitrostyrene catalysis by chiral aziridine-containing phosphines and phosphine oxides is described. Of the sixteen stereoisomers that could be formed as a result of the title reaction, three were formed, two of which were obtained in an enantiomerically enriched or pure form, and one in a racemic form. One of the products underwent epimerization under basic reaction conditions.

摘要

描述了由相应的亚氨基酯生成的甲亚胺叶立德与β-硝基苯乙烯在手性含氮丙啶的膦和氧化膦催化下的不对称[3+2]环加成反应。由于该标题反应可能形成16种立体异构体,其中三种形成了,其中两种以对映体富集或纯的形式获得,一种以外消旋形式获得。其中一种产物在碱性反应条件下发生差向异构化。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5360/11279481/61f0c0468713/molecules-29-03283-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5360/11279481/a6e425bff9af/molecules-29-03283-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5360/11279481/a13b35367d17/molecules-29-03283-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5360/11279481/d6d1243f6fa9/molecules-29-03283-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5360/11279481/602e2c150f71/molecules-29-03283-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5360/11279481/dd757590ca83/molecules-29-03283-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5360/11279481/f1f24d656106/molecules-29-03283-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5360/11279481/4e13ecc6b3c4/molecules-29-03283-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5360/11279481/61f0c0468713/molecules-29-03283-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5360/11279481/a6e425bff9af/molecules-29-03283-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5360/11279481/a13b35367d17/molecules-29-03283-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5360/11279481/d6d1243f6fa9/molecules-29-03283-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5360/11279481/602e2c150f71/molecules-29-03283-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5360/11279481/dd757590ca83/molecules-29-03283-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5360/11279481/f1f24d656106/molecules-29-03283-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5360/11279481/4e13ecc6b3c4/molecules-29-03283-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5360/11279481/61f0c0468713/molecules-29-03283-g004.jpg

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本文引用的文献

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Recent insights about pyrrolidine core skeletons in pharmacology.药理学中关于吡咯烷核心骨架的最新见解。
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Copper-Catalyzed Asymmetric Propargylic [3 + 2] Cycloaddition: Synthesis of Enantioenriched Dihydrofuro[3,2-]coumarins and its Quinolinone and Thiocoumarin Analogues.铜催化的不对称丙炔基[3 + 2]环加成反应:手性富集的二氢呋喃并[3,2-]香豆素及其喹啉酮和噻吩并香豆素类似物的合成。
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