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通过与手性助剂形成的非对映异构体实现均配型环金属化铱（III）配合物羧酸衍生物的光学拆分

Optical Resolution of Carboxylic Acid Derivatives of Homoleptic Cyclometalated Iridium(III) Complexes via Diastereomers Formed with Chiral Auxiliaries.

作者信息

Kanbe Azusa, Yokoi Kenta, Yamada Yasuyuki, Tsurui Makoto, Kitagawa Yuichi, Hasegawa Yasuchika, Ogata Daiji, Yuasa Junpei, Aoki Shin

机构信息

Faculty of Pharmaceutical Science, Tokyo University of Science, 2641 Yamazaki, Noda, Chiba 278-8510, Japan.

Department of Chemistry, Graduate School of Science, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8602, Japan.

出版信息

Inorg Chem. 2023 Jul 24;62(29):11325-11341. doi: 10.1021/acs.inorgchem.3c00685. Epub 2023 Jul 11.

DOI:10.1021/acs.inorgchem.3c00685
PMID:37432912
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10369494/
Abstract

We report on a facile method for the optical resolution of cyclometalated iridium(III) (Ir(III)) complexes via diastereomers formed with chiral auxiliaries. The racemic carboxylic acids of Ir(III) complexes (- (-Ir(ppyCOH) (ppy: 2-phenylpyridine)), - (-Ir(tpyCOH) (tpy: 2-(4'-tolyl)pyridine)), and - (-Ir(mpiqCOH) (mpiq: 1-(4'-methylphenyl)isoquinoline))) were converted into the diastereomers, Δ- and Λ-forms of - (from -), - (from -), - (from -), and - (from -), respectively, by the condensation with (12)-1,2-diaminocyclohexane or (12)-2-aminocyclohexanol. The resulting diastereomers were separated by HPLC (with a nonchiral column) or silica gel column chromatography, and their absolute stereochemistry was determined by X-ray single-crystal structure analysis and CD (circular dichroism) spectra. Spectra of all diastereomers of the Ir(III) complexes are reported. Hydrolysis of the ester moieties of Δ- and Λ-forms of -, -, and - gave both enantiomers of the corresponding carboxylic acid derivatives in the optically pure forms, Δ- and Λ--, -, and -, respectively.

摘要

我们报道了一种通过与手性助剂形成非对映异构体来对环金属化铱（III）（Ir(III)）配合物进行光学拆分的简便方法。Ir(III)配合物（-(-Ir(ppyCOH)（ppy：2-苯基吡啶））、-(-Ir(tpyCOH)（tpy：2-(4'-甲苯基)吡啶））和-(-Ir(mpiqCOH)（mpiq：1-(4'-甲基苯基)异喹啉）））的外消旋羧酸分别通过与(12)-1,2-二氨基环己烷或(12)-2-氨基环己醇缩合，转化为-（来自-）、-（来自-）、-（来自-）和-（来自-）的Δ-和Λ-形式的非对映异构体。所得非对映异构体通过HPLC（使用非手性柱）或硅胶柱色谱法分离，其绝对立体化学通过X射线单晶结构分析和CD（圆二色性）光谱确定。报道了Ir(III)配合物所有非对映异构体的光谱。-、-和-的Δ-和Λ-形式的酯部分水解分别得到相应羧酸衍生物的两种对映体，即光学纯形式的Δ-和Λ--、-和-。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9ce2/10369494/3e67a2ff041c/ic3c00685_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9ce2/10369494/66bf50d710b8/ic3c00685_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9ce2/10369494/cc8188f54683/ic3c00685_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9ce2/10369494/f1f4fd37fb86/ic3c00685_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9ce2/10369494/46a5464a489a/ic3c00685_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9ce2/10369494/6bba960253ea/ic3c00685_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9ce2/10369494/a75dc2e1ca74/ic3c00685_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9ce2/10369494/70ab9fe2241c/ic3c00685_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9ce2/10369494/d97f9a3a935d/ic3c00685_0009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9ce2/10369494/b9abf7c1685f/ic3c00685_0010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9ce2/10369494/3e67a2ff041c/ic3c00685_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9ce2/10369494/66bf50d710b8/ic3c00685_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9ce2/10369494/cc8188f54683/ic3c00685_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9ce2/10369494/f1f4fd37fb86/ic3c00685_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9ce2/10369494/46a5464a489a/ic3c00685_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9ce2/10369494/6bba960253ea/ic3c00685_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9ce2/10369494/a75dc2e1ca74/ic3c00685_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9ce2/10369494/70ab9fe2241c/ic3c00685_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9ce2/10369494/d97f9a3a935d/ic3c00685_0009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9ce2/10369494/b9abf7c1685f/ic3c00685_0010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9ce2/10369494/3e67a2ff041c/ic3c00685_0004.jpg

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