Critical role of Bronsted acid in Lewis-acid-catalyzed synthesis of Amadori and Heyns compounds of β-amino acids. Issue 22 (17th November 2021)

• Record Type: Journal Article
• Authors: Chanda, Debasree; Venkataswamy, Gangothri M.; Hipparagi, Lagamawwa V.; Harohally, Nanishankar V.
• Is Part Of: Synthetic communications. Volume 51:Issue 22(2021)
• Page Start: 3379
• Page End: 3389
• Publication Date: 2021-11-17
• Subjects: Amadori reaction -- Heyns reaction -- β-amino acids -- Lewis acid -- Bronsted acid -- Catalysis; Organic compounds -- Synthesis -- Periodicals; Chemistry, Organic; Synthesis; 547.205
• DOI: 10.1080/00397911.2021.1971718
• Languages: English
• ISSNs: 0039-7911

Abstract

Abstract: Amadori and Heyns rearrangement reactions are a century old reactions of the carbohydrates. The great body of literature on these reactions are concentrated on ɑ-amino acids. Reports on the synthesis and chemistry of Amadori and Heyns compounds derived from β-amino acids are scarce. We demonstrate herein, via Lewis-acid catalysis, synthesis of Amadori and Heyns compounds derived from β-amino acids consisting of β-alanine and β-phenylalanine with, D-xylose, D-galactose, D-fructose, D-mannose, D-maltose, D-lactose. The accomplished Lewis-acid catalyzed method is practical and devoid of separation techniques for achieving purity. We also report insight on the mechanism of Lewis-acid catalyzed Amadori and Heyns rearrangement reactions, and reveal the key role of Bronsted acid in Lewis-acid catalyzed Amadori and Heyns synthesis of β-amino acids. Graphical Abstract: UF0001