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手性单膦配体促进的 Ru 催化芳基硼酸对脂肪醛的不对称加成反应。

Ru-Catalyzed Asymmetric Addition of Arylboronic Acids to Aliphatic Aldehydes via -Chiral Monophosphorous Ligands.

机构信息

School of Pharmacy, Gannan Medical University, Ganzhou 341000, China.

College of Chemistry and Environmental Engineering, Shaoguan University, Shaoguan 512005, China.

出版信息

Molecules. 2022 Jun 17;27(12):3898. doi: 10.3390/molecules27123898.

DOI:10.3390/molecules27123898
PMID:35745017
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9231018/
Abstract

Chiral alcohols are among the most widely applied in fine chemicals, pharmaceuticals and agrochemicals. Herein, the Ru-monophosphine catalyst formed in situ was found to promote an enantioselective addition of aliphatic aldehydes with arylboronic acids, delivering the chiral alcohols in excellent yields and enantioselectivities and exhibiting a broad scope of aliphatic aldehydes and arylboronic acids. The enantioselectivities are highly dependent on the monophosphorous ligands. The utility of this asymmetric synthetic method was showcased by a large-scale transformation.

摘要

手性醇是精细化学品、制药和农用化学品中应用最广泛的化合物之一。在此,我们发现原位形成的钌-单膦催化剂可以促进脂肪族醛与芳基硼酸的对映选择性加成,以优异的收率和对映选择性得到手性醇,并具有广泛的脂肪族醛和芳基硼酸的适用范围。对映选择性高度依赖于单磷配体。该不对称合成方法的实用性通过大规模转化得到了展示。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6c20/9231018/7ccc9e130302/molecules-27-03898-sch009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6c20/9231018/c2a3cc4c7e73/molecules-27-03898-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6c20/9231018/805347a02ad7/molecules-27-03898-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6c20/9231018/2a9dbd46d6c9/molecules-27-03898-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6c20/9231018/deab064eba15/molecules-27-03898-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6c20/9231018/266d57dd55ab/molecules-27-03898-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6c20/9231018/dfff1ed9fc2e/molecules-27-03898-sch006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6c20/9231018/216752872e38/molecules-27-03898-sch007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6c20/9231018/5f1cf24eda70/molecules-27-03898-sch008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6c20/9231018/7ccc9e130302/molecules-27-03898-sch009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6c20/9231018/c2a3cc4c7e73/molecules-27-03898-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6c20/9231018/805347a02ad7/molecules-27-03898-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6c20/9231018/2a9dbd46d6c9/molecules-27-03898-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6c20/9231018/deab064eba15/molecules-27-03898-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6c20/9231018/266d57dd55ab/molecules-27-03898-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6c20/9231018/dfff1ed9fc2e/molecules-27-03898-sch006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6c20/9231018/216752872e38/molecules-27-03898-sch007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6c20/9231018/5f1cf24eda70/molecules-27-03898-sch008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6c20/9231018/7ccc9e130302/molecules-27-03898-sch009.jpg

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Nickel-Catalyzed Guerbet Type Reaction: C-Alkylation of Secondary Alcohols Double (de)Hydrogenation.
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Angew Chem Int Ed Engl. 2021 Apr 26;60(18):9978-9983. doi: 10.1002/anie.202101668. Epub 2021 Mar 17.
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