Asymmetric Aldol “Reaction in Water” Using Ferrocene-Amino Acid Conjugates

化学 催化作用 二茂铁 羟醛反应 氨基酸 分子内力 圆二色性 药物化学 立体化学 咪唑 有机化学 电极 电化学 生物化学 物理化学
作者
Lo’ay Al-Momani,Anas Lataifeh
出处
期刊:Industrial & Engineering Chemistry Research [American Chemical Society]
卷期号:61 (6): 2417-2424 被引量:4
标识
DOI:10.1021/acs.iecr.1c04725
摘要

This article reports an array of water-compatible organocatalysts. The precatalysts are based on ferrocene (Fc) conjugates of l-amino acids having the general formula Fc[C(O)–O-aa-OBz]n and Fc[C(O)–NH-Z-Lys-Obz]n; aa = 4-trans-Z-Hyp, 4-cis-Z-Hyp, and Z-Ser; n = 1, 2; Z = benzyloxy carbonyl, Bz = benzylic; Hyp = hydroxyproline, Ser = Serine, and Lys = Lysine. The Fc is coupled to the amino acids through the functional group that resides in the amino acid side chain, while the α-amine and α-carboxyl groups are protected by Z and Bz moieties, respectively. The removal of protecting groups affords the Fc catalysts. Circular dichroism (CD) of disubstituted Fc-Hyp amino acid precatalysts displays an induced helical chirality at the Fc region of the spectra due to the π–π interactions of the aromatic Z and Bz groups, while disubstituted Fc-precatalysts of Ser and Lys show a positive Cotton effect as a result of intramolecular, interstrand H-bonding, and π–π interactions. The disubstituted Fc catalysts were CD “silent”. The studied catalysts promote asymmetric aldol of 4-nitrobenzaldehyde with acetone in water (>70 equiv) at 20 mol % catalyst loading. The catalytic conversion and enantioselectivities (ee) of the control catalysts follow the order Pro ≈ Hyp > Ser > Lys. The monosubstituted Fc catalysts display good conversions (30–90)% and ee (50–80)% and follow a similar decreasing order to their respective control catalysts. The ee of these catalysts outperforms their corresponding control. The disubstituted Fc catalysts express both low conversions and ee. The catalytic behavior of the catalysts is rationalized by both a “hydrophobic” effect and the amino acid propensity to form zwitterions in water at pH ∼ 7.
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