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通过镍催化醛与保护的氨基戊二烯酸酯的还原偶联对 - 氨基醇衍生物进行对映选择性合成。

Enantioselective Synthesis of -Aminoalcohol Derivatives by Nickel-Catalyzed Reductive Coupling of Aldehydes with Protected Amino-pentadienoates.

作者信息

Bender Thilo, Fürstner Alois

机构信息

Max-Planck-Institut für Kohlenforschung, 45470 Mülheim/Ruhr, Germany.

出版信息

J Am Chem Soc. 2024 Dec 11;146(49):33295-33301. doi: 10.1021/jacs.4c12002. Epub 2024 Nov 22.

DOI:10.1021/jacs.4c12002
PMID:39576228
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11638964/
Abstract

A VAPOL-derived phosphoramidite ligand is uniquely effective at reverting the regiochemical course of nickel-catalyzed reactions of aldehydes with carbamate-protected 5-amino-2,4-pentadienoates as "push/pull" dienes; the ensuing carbonyl α-amino-homoallylation reaction affords -configured -aminoalcohol derivatives in good yields with high optical purity. The reductive coupling is conveniently performed with a bench-stable Ni(0) precatalyst and EtB as the promoter.

摘要

一种源自VAPOL的亚磷酰胺配体在逆转镍催化的醛与氨基甲酸酯保护的5-氨基-2,4-戊二烯酸酯作为“推/拉”二烯的反应的区域化学过程方面具有独特的效果；随后的羰基α-氨基高烯丙基化反应以高光学纯度的良好产率提供了构型的α-氨基醇衍生物。还原偶联反应使用易于在实验台上稳定保存的Ni(0)预催化剂和EtB作为促进剂方便地进行。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6148/11638964/3fb57f0d9da8/ja4c12002_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6148/11638964/469600f94fc4/ja4c12002_0003.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6148/11638964/b73b53547624/ja4c12002_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6148/11638964/5f3f9f96f55a/ja4c12002_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6148/11638964/714cfb4977ac/ja4c12002_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6148/11638964/83c7c575fb51/ja4c12002_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6148/11638964/3fb57f0d9da8/ja4c12002_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6148/11638964/469600f94fc4/ja4c12002_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6148/11638964/2c6d0b5432a4/ja4c12002_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6148/11638964/ac2d99fa15cb/ja4c12002_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6148/11638964/b73b53547624/ja4c12002_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6148/11638964/5f3f9f96f55a/ja4c12002_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6148/11638964/714cfb4977ac/ja4c12002_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6148/11638964/83c7c575fb51/ja4c12002_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6148/11638964/3fb57f0d9da8/ja4c12002_0008.jpg

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