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通过对伊文斯恶唑烷酮部分进行立体定向烷基化反应制备光学纯杯芳烃膦

Optically Pure Calixarenyl Phosphine via Stereospecific Alkylation on Evans' Oxazolidinone Moiety.

作者信息

Bauder Claude, Sémeril David

机构信息

Synthèse Organométallique et Catalyse, UMR-CNRS 7177 Institut de Chimie de Strasbourg, Strasbourg University, 67008 Strasbourg, France.

出版信息

Molecules. 2024 Mar 5;29(5):1156. doi: 10.3390/molecules29051156.

DOI:10.3390/molecules29051156
PMID:38474667
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10934826/
Abstract

A convenient protocol for the synthesis of 25,26,27-tribenzoyl-28-[(()-1-diphenylphos- phanyl-propan-2-yl)oxy]-calix[4]arene via stereospecific methylation on Evans' oxazolidinone moiety was reported. According to the C NMR analysis of this phosphine, the calix[4]arene skeleton adopted a 1,3-alternate conformation. The latter conformation of the macrocycle and the ()-chirality of the carbon atom bearing the methyl substituent were confirmed by a single-crystal X-ray diffraction study. After coordination of the phosphinated ligand to the dimeric [RuCl(-cymene)] organometallic precursor, the resulting arene-ruthenium complex was tested in the asymmetric reduction of acetophenone and alcohol was obtained with modest enantiomeric excess.

摘要

报道了一种通过对伊文斯恶唑烷酮部分进行立体定向甲基化来合成25,26,27-三苯甲酰基-28-[（（）-1-二苯基膦基-丙-2-基）氧基]-杯[4]芳烃的简便方法。根据该膦的碳核磁共振分析，杯[4]芳烃骨架呈1,3-交替构象。通过单晶X射线衍射研究证实了大环的后一种构象以及带有甲基取代基的碳原子的（）-手性。在将膦化配体与二聚体[RuCl（-对异丙基苯）]有机金属前体配位后，所得芳烃-钌配合物用于苯乙酮的不对称还原测试，并以适度的对映体过量获得了醇。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c316/10934826/c85230cc3694/molecules-29-01156-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c316/10934826/021dfa3cbbf4/molecules-29-01156-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c316/10934826/de38258d26fe/molecules-29-01156-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c316/10934826/1a307a4fd04b/molecules-29-01156-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c316/10934826/e2d0fe44afcc/molecules-29-01156-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c316/10934826/14a592a96c30/molecules-29-01156-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c316/10934826/69bbd1ef8b7d/molecules-29-01156-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c316/10934826/8ef6864d0c69/molecules-29-01156-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c316/10934826/40832b2004e7/molecules-29-01156-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c316/10934826/c85230cc3694/molecules-29-01156-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c316/10934826/021dfa3cbbf4/molecules-29-01156-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c316/10934826/de38258d26fe/molecules-29-01156-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c316/10934826/1a307a4fd04b/molecules-29-01156-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c316/10934826/e2d0fe44afcc/molecules-29-01156-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c316/10934826/14a592a96c30/molecules-29-01156-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c316/10934826/69bbd1ef8b7d/molecules-29-01156-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c316/10934826/8ef6864d0c69/molecules-29-01156-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c316/10934826/40832b2004e7/molecules-29-01156-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c316/10934826/c85230cc3694/molecules-29-01156-sch003.jpg

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4
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5
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6
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Materials (Basel). 2022 Aug 23;15(17):5812. doi: 10.3390/ma15175812.
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Chemistry. 2018 Feb 6;24(8):1744-1754. doi: 10.1002/chem.201703367. Epub 2017 Dec 11.
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Acta Crystallogr C Struct Chem. 2015 Jan;71(Pt 1):3-8. doi: 10.1107/S2053229614024218. Epub 2015 Jan 1.
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SHELXT - integrated space-group and crystal-structure determination.SHELXT——集成空间群与晶体结构测定
Acta Crystallogr A Found Adv. 2015 Jan;71(Pt 1):3-8. doi: 10.1107/S2053273314026370. Epub 2015 Jan 1.
10
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European J Org Chem. 2013 Jul 1;2013(20). doi: 10.1002/ejoc.201300643.