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钯催化含烯丙基的α-氨基酸衍生物与末端炔烃的区域选择性氢烷氧基化反应

Regioselective Pd-Catalyzed Hydroalkynylation of Allenyl-Containing α-Amino Acid Derivatives with Terminal Alkynes.

作者信息

Bubnova Alexandra S, Vorobyeva Daria V, Godovikov Ivan A, Philippova Anna N, Gribanov Pavel S, Antoshkina Evgenia P, Osipov Sergey N

机构信息

A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28/1 Vavilova Str., 119334 Moscow, Russia.

出版信息

Molecules. 2025 Sep 4;30(17):3623. doi: 10.3390/molecules30173623.

DOI:10.3390/molecules30173623
PMID:40942148
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12430138/
Abstract

An efficient access to the novel representatives of α,α-disubstituted α-amino acids with 1,3-enyne unit located at their side chain has been elaborated. The method is based on Pd(II)-catalyzed hydroalkynylation of α-allenyl-α-dimethylamino esters with terminal acetylenes. The developed strategy is the first example of the metal-catalyzed allene-alkyne coupling to provide a convenient route to new unsaturated α-amino acid derivatives in good yields and high selectivity.

摘要

已详细阐述了一种有效合成新型α,α-二取代α-氨基酸的方法,这些氨基酸的侧链带有1,3-烯炔单元。该方法基于钯(II)催化的α-烯丙基-α-二甲基氨基酯与末端乙炔的氢炔基化反应。所开发的策略是金属催化的丙二烯-炔烃偶联反应的首个实例,为高产率和高选择性地制备新型不饱和α-氨基酸衍生物提供了一条便捷途径。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e59/12430138/0dc6dd92d54c/molecules-30-03623-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e59/12430138/febeeacc7d09/molecules-30-03623-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e59/12430138/67ce549b5c16/molecules-30-03623-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e59/12430138/3db1849f1aa4/molecules-30-03623-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e59/12430138/46cc88d3e506/molecules-30-03623-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e59/12430138/0dc6dd92d54c/molecules-30-03623-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e59/12430138/febeeacc7d09/molecules-30-03623-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e59/12430138/67ce549b5c16/molecules-30-03623-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e59/12430138/3db1849f1aa4/molecules-30-03623-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e59/12430138/46cc88d3e506/molecules-30-03623-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e59/12430138/0dc6dd92d54c/molecules-30-03623-sch005.jpg

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本文引用的文献

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Stereodivergent access to non-natural α-amino acids via enantio- and /-selective catalysis.通过对映选择性和/或非对映选择性催化实现非天然α-氨基酸的立体发散合成。
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Preparation of ()-1,3-Enyne Derivatives through Palladium Catalyzed Hydroalkynylation of Allenes.通过钯催化烯丙基的氢炔基化反应制备 ()-1,3-烯炔衍生物。
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