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Title: Directed Cu(I)-catalyzed carbomagnesiation of 1-arylcycloprop-2-ene-1-carboxamides en route to densely substituted functionalized cyclopropanes
Authors: Rubin, M. A.
Рубин, М. А.
Keywords: Amide functionalities;Carbomagnesiation;Copper catalyzed;Diastereo-selectivity;Directing groups;Efficient control;Grignard reagent
Issue Date: 2018
Publisher: American Chemical Society
Citation: Edwards, A., Rubin, M. Directed Cu(I)-Catalyzed Carbomagnesiation of 1-Arylcycloprop-2-ene-1-carboxamides en Route to Densely Substituted Functionalized Cyclopropanes // Journal of Organic Chemistry. - 2018. - Volume 83. - Issue 15. - Pages 8426-8448
Series/Report no.: Journal of Organic Chemistry
Abstract: Copper-catalyzed, directed addition of Grignard reagents across the strained C=C bond of cyclopropene-3-carboxamides was developed. It was demonstrated that the amide functionality serves as an ultimate directing group allowing for highly efficient control of diastereoselectivity of addition including stereoselectivity of electrophilic trapping with prochiral aldehydes. Also, regioselectivity of carbomagnesiation of cyclopropenes with a monosubstituted double bond is investigated. It was shown that in many cases this selectivity is controlled by steric factors and allows for preparation of products with a "reversed" regiochemistry
Appears in Collections:Статьи, проиндексированные в SCOPUS, WOS

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