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对映选择性铁/双喹啉二胺配体催化的 2-萘酚氧化偶联反应。

Enantioselective Iron/Bisquinolyldiamine Ligand-Catalyzed Oxidative Coupling Reaction of 2-Naphthols.

机构信息

Sauvage Center for Molecular Sciences, Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei 430072, China.

出版信息

Molecules. 2020 Feb 14;25(4):852. doi: 10.3390/molecules25040852.

DOI:10.3390/molecules25040852
PMID:32075144
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7070846/
Abstract

An iron-catalyzed asymmetric oxidative homo-coupling of 2-naphthols for the synthesis of 1,1'-Bi-2-naphthol (BINOL) derivatives is reported. The coupling reaction provides enantioenriched BINOLs in good yields (up to 99%) and moderate enantioselectivities (up to 81:19 er) using an iron-complex generated in situ from Fe(ClO) and a bisquinolyldiamine ligand [(1,2)-,-di(quinolin-8-yl)cyclohexane-1,2-diamine, ]. A number of ligands (-) and the analogs of , with various substituents and chiral backbones, were synthesized and examined in the oxidative coupling reactions.

摘要

报道了一种铁催化的 2-萘酚不对称氧化偶联反应,用于合成 1,1'-联萘-2,2'-二醇(BINOL)衍生物。该偶联反应使用原位生成的铁配合物[Fe(ClO)]和双喹啉二胺配体[(1,2)-,-二(喹啉-8-基)环己烷-1,2-二胺],以良好的收率(高达 99%)和中等的对映选择性(高达 81:19 er)得到了手性富集的 BINOL。合成了一系列配体(-)和类似物 ,具有各种取代基和手性骨架,并在氧化偶联反应中进行了测试。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/15f7/7070846/beffae272b28/molecules-25-00852-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/15f7/7070846/3ddda5e00065/molecules-25-00852-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/15f7/7070846/225c64216a63/molecules-25-00852-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/15f7/7070846/88104bef6b0d/molecules-25-00852-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/15f7/7070846/d40387682402/molecules-25-00852-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/15f7/7070846/098728f0fba2/molecules-25-00852-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/15f7/7070846/939782257899/molecules-25-00852-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/15f7/7070846/8496bb06a79b/molecules-25-00852-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/15f7/7070846/beffae272b28/molecules-25-00852-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/15f7/7070846/3ddda5e00065/molecules-25-00852-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/15f7/7070846/225c64216a63/molecules-25-00852-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/15f7/7070846/88104bef6b0d/molecules-25-00852-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/15f7/7070846/d40387682402/molecules-25-00852-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/15f7/7070846/098728f0fba2/molecules-25-00852-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/15f7/7070846/939782257899/molecules-25-00852-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/15f7/7070846/8496bb06a79b/molecules-25-00852-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/15f7/7070846/beffae272b28/molecules-25-00852-sch005.jpg

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