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钯催化的羰基和亚胺连接的亚烷基环丙烷的串联环异构化/交叉偶联反应

Palladium-Catalyzed Tandem Cycloisomerization/Cross-Coupling of Carbonyl- and Imine-Tethered Alkylidenecyclopropanes.

作者信息

Verdugo Felipe, Rodiño Ricardo, Calvelo Martín, Mascareñas José Luis, López Fernando

机构信息

Centro Singular de Investigación en Química Biolóxica e Materiais Moleculares (CIQUS) and Departamento de Química Orgánica, Universidad de Santiago de Compostela, Spain.

Misión Biológica de Galicia (MBG), Consejo, Superior de Investigaciones Científicas (CSIC), 36680, Pontevedra, Spain.

出版信息

Angew Chem Int Ed Engl. 2022 Jun 13;61(24):e202202295. doi: 10.1002/anie.202202295. Epub 2022 Apr 14.

DOI:10.1002/anie.202202295
PMID:35348273
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9324954/
Abstract

Pd catalysts featuring phosphorus-based monodentate ligands can detour the reactivity of carbonyl-tethered alkylidenecyclopropanes (ACPs) from standard (3+2) cycloadditions towards tandem cycloisomerization/cross-coupling processes. This new reactivity lies on the formation of key π-allyl oxapalladacyclic intermediates, which are subsequently trapped with external nucleophilic partners, instead of undergoing canonical C-O reductive eliminations. Importantly, the use of imine-tethered ACP's is also feasible. Therefore, the method provides a straightforward and stereoselective entry to a wide variety of highly functionalized cyclic alcohols and amines.

摘要

具有磷基单齿配体的钯催化剂可使羰基连接的亚烷基环丙烷（ACP）的反应性从标准的（3+2）环加成反应转向串联环异构化/交叉偶联过程。这种新的反应性基于关键的π-烯丙基氧杂钯环中间体的形成，这些中间体随后被外部亲核试剂捕获，而不是进行常规的C-O还原消除反应。重要的是，使用亚胺连接的ACP也是可行的。因此，该方法为合成各种高度官能化的环醇和胺提供了一种直接且立体选择性的途径。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4f8d/9324954/95e6ad6ff7c2/ANIE-61-0-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4f8d/9324954/147a339e83f6/ANIE-61-0-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4f8d/9324954/971329e05aa1/ANIE-61-0-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4f8d/9324954/27336e188e2c/ANIE-61-0-g003.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4f8d/9324954/95e6ad6ff7c2/ANIE-61-0-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4f8d/9324954/147a339e83f6/ANIE-61-0-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4f8d/9324954/971329e05aa1/ANIE-61-0-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4f8d/9324954/27336e188e2c/ANIE-61-0-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4f8d/9324954/440f56bd62dc/ANIE-61-0-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4f8d/9324954/95e6ad6ff7c2/ANIE-61-0-g007.jpg

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