Synthesis of (E)‐Enaminoesters by a 1,6‐Addition/Fragmentation Cascade Involving Coumalic Acid Esters and Secondary Amines

Author:

Xavier Tania1,Condon Sylvie1,Pichon Christophe1,Le Gall Erwan1ORCID,Presset Marc1ORCID

Affiliation:

1. Univ Paris Est Creteil, CNRS, ICMPE, UMR 7182 2 rue Henri Dunant 94320 Thiais France

Abstract

AbstractCoumalic 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.

Publisher

Wiley

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