Decarboxylative Mannich Reactions with Substituted Malonic Acid Half-Oxyesters

Tania Xavier; Sylvie Condon; Christophe Pichon; Erwan Le Gall; Marc Presset

doi:10.1021/acs.joc.0c02895

Decarboxylative Mannich Reactions with Substituted Malonic Acid Half-Oxyesters

J Org Chem. 2021 Apr 16;86(8):5452-5462. doi: 10.1021/acs.joc.0c02895. Epub 2021 Apr 6.

Authors

Tania Xavier¹, Sylvie Condon¹, Christophe Pichon¹, Erwan Le Gall¹, Marc Presset¹

Affiliation

¹ ICMPE, Université Paris Est Créteil, CNRS, ICMPE, UMR7182, 2 rue Henri Dunant, F-94320 Thiais, France.

PMID: 33822615
DOI: 10.1021/acs.joc.0c02895

Abstract

The decarboxylative Mannich reaction between imines and substituted malonic acids half-oxyesters (SMAHOs) has been developed using 1,4-diazabicyclo[2.2.2]octane (DABCO) as an organocatalyst. The reaction proceeds under simple reaction conditions and tolerates a broad range of substrates, affording general access to β^2,3-aminoesters, the syn diastereomer being the major one. An alternative multicomponent protocol has also been developed to increase the overall eco-compatibility of the process.

Publication types

Research Support, Non-U.S. Gov't