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Synthesis of (E)‐Enaminoesters by a 1,6‐Addition/Fragmentation Cascade Involving Coumalic Acid Esters and Secondary Amines.
- Source :
-
European Journal of Organic Chemistry . 8/19/2024, Vol. 27 Issue 31, p1-4. 4p. - Publication Year :
- 2024
-
Abstract
- Coumalic acid methyl ester (methyl coumalate), a biomass‐derived building block, was converted into (E)‐enaminoesters by an original uncatalyzed stereoselective 1,6‐addition/fragmentation cascade involving secondary amines. The transformation occurred under useful experimental conditions as a simple heating of a stoichiometric mixture of the starting compounds led to the desired products. The reaction could be extended to a range of alkyl coumalates and a variety of secondary amines. Given the original character of the transformation, the reaction mechanism was discussed. Therefore, the cascade is supposed to involve a 1,6‐conjugate addition followed by a fragmentation sequence leading ultimately to the decarboxylative elimination of (E)‐enaminoesters. Using this procedure, renewable coumalic acid proved to be a valuable alternative to fossil fuel‐based propiolates for the preparation of enaminoesters. [ABSTRACT FROM AUTHOR]
- Subjects :
- *SECONDARY amines
*METHYL formate
*NUCLEOPHILIC reactions
*ESTERS
*HEATING
Subjects
Details
- Language :
- English
- ISSN :
- 1434193X
- Volume :
- 27
- Issue :
- 31
- Database :
- Academic Search Index
- Journal :
- European Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 179109712
- Full Text :
- https://doi.org/10.1002/ejoc.202400435