Enantioselective Synthesis of Chromanones Bearing an α,α-Disubstituted α-Amino Acid Moiety via Decarboxylative Michael Reaction

Jan Bojanowski; Lesław Sieroń; Anna Albrecht

doi:10.3390/molecules24142565

Enantioselective Synthesis of Chromanones Bearing an α,α-Disubstituted α-Amino Acid Moiety via Decarboxylative Michael Reaction

Molecules. 2019 Jul 15;24(14):2565. doi: 10.3390/molecules24142565.

Authors

Jan Bojanowski¹, Lesław Sieroń², Anna Albrecht³

Affiliations

¹ Institute of Organic Chemistry, Faculty of Chemistry, Lodz University of Technology, Żeromskiego 116, 90-924 Łódź, Poland.
² Institute of General and Ecological Chemistry, Faculty of Chemistry, Lodz University of Technology, Żeromskiego 116, 90-924 Łódź, Poland.
³ Institute of Organic Chemistry, Faculty of Chemistry, Lodz University of Technology, Żeromskiego 116, 90-924 Łódź, Poland. anna.albrecht@p.lodz.pl.

Abstract

In this manuscript, a novel, decarboxylative Michael reaction between α-substituted azlactones and chromone-3-carboxylic acids is described. The reaction proceeds in a sequence Michael addition followed by decarboxylative deprotonation, and it results in the formation of chromanones bearing an azlactone structural unit. The possibility of transforming an azlactone moiety into a protected α,α-disubstituted α-amino acid derivative is also demonstrated.

Keywords: Michael addition; azlactones; decarboxylation; organocatalysis; α,α-disubstituted α-amino acids.

MeSH terms

Chromones / chemical synthesis*
Chromones / chemistry
Cycloaddition Reaction
Decarboxylation
Molecular Structure
Stereoisomerism

Substances

Chromones

Grants and funding

UMO-2016/21/D/ST5/01668/Narodowe Centrum Nauki