![4-[(2-{2-[2-(2-Aminoethoxy)ethoxy]ethoxy}ethyl)amino]-2-(2,6-dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione structure](https://static.chemtradehub.com/structs/209/2093416-31-8-3162.webp "4-[(2-{2-[2-(2-Aminoethoxy)ethoxy]ethoxy}ethyl)amino]-2-(2,6-dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione structure")
4-[(2-{2-[2-(2-Aminoethoxy)ethoxy]ethoxy}ethyl)amino]-2-(2,6-dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione
CAS Number:
2093416-31-8
Molecular Formula:
C21H28N4O7
Asymmetric copper-catalyzed alkynylallylic dimethylamination
Literature Information
Publication Date
2023-12-05
DOI
10.1039/D3QO01749D
Impact Factor
5.281
Authors
View Original
Abstract
A feasible protocol for Cu-catalyzed asymmetric alkynylallylic dimethylamination is developed with the discovery of tetramethyldiaminomethane as a new, stable and convenient surrogate of dimethylamine. A series of enantioenriched 1,4-enynes are constructed in reasonable yields, high regioselectivities and moderate to good enantioselectivities. Mechanistic experiments show that the tertiary amine works as a nucleophile directly followed by the release of the expected dialkylamine unit, different from the conventional primary and secondary amines with the cleavage of a proton as the nucleophile. DFT calculations elucidate the origin of regio- and enantioselectivity for the present transformation.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
5,5',5''-(((2,4,6-Trimethylbenzene-1,3,5-triyl)tris(methylene))tris(oxy))triisophthalic acid
CAS Number:
1159974-70-5
Molecular Formula:
C36H30O15
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