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膦催化2-(溴甲基)丙烯酸酯向1,2-双(环己烯基)乙烯基衍生物的区域和立体选择性多米诺六聚化反应

Phosphine-Catalyzed Domino Regio- and Stereo-Selective Hexamerization of 2-(Bromomethyl)acrylates to 1,2-Bis(cyclohexenyl)ethenyl Derivatives.

作者信息

Papis Marta, Bucci Raffaella, Contini Alessandro, Gelmi Maria Luisa, Lo Presti Leonardo, Poli Giovanni, Broggini Gianluigi, Loro Camilla

机构信息

Dipartimento di Scienza e Alta Tecnologia, Università degli Studi dell'Insubria, Via Valleggio 9, 22100, Como, Italy.

Dipartimento di Scienze Farmaceutiche, DISFARM Università degli Studi di Milano, Via Venezian 21, 20133, Milano, Italy.

出版信息

Org Lett. 2023 Oct 13;25(40):7380-7384. doi: 10.1021/acs.orglett.3c02836. Epub 2023 Sep 29.

DOI:10.1021/acs.orglett.3c02836
PMID:37772494
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10580324/
Abstract

A phosphine-catalyzed domino assembly of six units of 2-bromomethyl acrylates afforded polyalkenyl adducts containing two cyclohexenyl rings. This reaction occurs under mild conditions providing the final product by formation of seven carbon-carbon bonds and four stereocenters. Experimental and computational studies support an initial dimerization of the substrate, which in turn trimerizes involving two totally regio- and stereocontrolled Diels-Alder cycloadditions. The yield of the hexamerization of the 2-bromomethyl acrylates depends on the size of the ester function. The protocol has also proved to be practicable on a gram scale.

摘要

膦催化的六个单元的2-溴甲基丙烯酸酯的多米诺组装反应得到了含有两个环己烯基环的聚烯基加合物。该反应在温和条件下发生，通过形成七个碳-碳键和四个立体中心得到最终产物。实验和计算研究支持底物的初始二聚化，进而三聚化，涉及两个完全区域和立体控制的狄尔斯-阿尔德环加成反应。2-溴甲基丙烯酸酯的六聚化产率取决于酯官能团的大小。该方法在克级规模上也已证明是可行的。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1f8e/10580324/39fa338c7718/ol3c02836_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1f8e/10580324/e6dcb0213ac0/ol3c02836_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1f8e/10580324/2d43774483bd/ol3c02836_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1f8e/10580324/097ca633b91c/ol3c02836_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1f8e/10580324/e6fa2853f669/ol3c02836_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1f8e/10580324/e786813691f4/ol3c02836_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1f8e/10580324/2ebe3cd7939f/ol3c02836_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1f8e/10580324/39fa338c7718/ol3c02836_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1f8e/10580324/e6dcb0213ac0/ol3c02836_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1f8e/10580324/2d43774483bd/ol3c02836_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1f8e/10580324/097ca633b91c/ol3c02836_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1f8e/10580324/e6fa2853f669/ol3c02836_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1f8e/10580324/e786813691f4/ol3c02836_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1f8e/10580324/2ebe3cd7939f/ol3c02836_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1f8e/10580324/39fa338c7718/ol3c02836_0001.jpg

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