Both Amide-Bearing α- and β-Amino Acids from Natural Aspartic Acid Are Efficient Organocatalysts for Enantioselective Aldol Reactions

Gen-Fa Wen; Rui Zhang; Chu-Yu Zhang; Chao-Shan Da

doi:10.1055/a-1953-1656

Synthesis, Inhaltsverzeichnis

Synthesis 2023; 55(04): 670-682
DOI: 10.1055/a-1953-1656

paper

Both Amide-Bearing α- and β-Amino Acids from Natural Aspartic Acid Are Efficient Organocatalysts for Enantioselective Aldol Reactions

Gen-Fa Wen‡

^aInstitute of Biochemistry and Molecular Biology, School of Life Sciences, Key Lab of Preclinical Study for New Drugs of Gansu Province, Lanzhou University, Lanzhou 730000, P. R. of China

,

Rui Zhang‡

^aInstitute of Biochemistry and Molecular Biology, School of Life Sciences, Key Lab of Preclinical Study for New Drugs of Gansu Province, Lanzhou University, Lanzhou 730000, P. R. of China

,

Chu-Yu Zhang

^bCuiying Honors College, Lanzhou University, Lanzhou 730000, P. R. of China

,

Chao-Shan Da ∗

^aInstitute of Biochemistry and Molecular Biology, School of Life Sciences, Key Lab of Preclinical Study for New Drugs of Gansu Province, Lanzhou University, Lanzhou 730000, P. R. of China

› Institutsangaben

Abstract

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Abstract

This work aims to compare and explore the different catalytic efficiencies of structurally similar α- and β-amino acids in an asymmetric aldol transformation. Interestingly, aspartic acid is not only an α-amino acid, but also a β-amino acid. Thus, by modifying one of the two acidic groups of aspartic acid, two sets of α- and β-amino acids, 14 amino acids in total, were prepared and used as organocatalysts. The two types of amino acid, interestingly, achieved similar high catalytic efficiencies in the asymmetric aldol transformation under different optimal conditions. The ideal β-amino acid, in some cases, even achieved significantly higher enantioselectivity than the ideal α-amino acid, although α-amino acids are extensively demonstrated to be highly efficient organocatalysts in this asymmetric transformation.

Key words

asymmetric catalysis - organocatalysis - α-amino acids - β-amino acids - aspartic acid - aldol reaction

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