Synthesis of Unnatural Amino Acid Derivatives by Visible- Light-Catalyzed Decarboxylative Alkylation of N-Aromatic Glyoxylimines

doi:10.6023/cjoc202304020

Abstract

A visible-light-mediated decarboxylative radical alkylation of glyoxylimines for preparing α-alkylated unnatural amino acid derivatives was developed. Various alkyl radicals generated by tetrachloro-N-hydroxyphthalimide (TCNHPI) active esters were added to imines in good yields under visible light irradiation. Iridium complex was selected as photocatalyst and also, Hantzsch ester (HE) as hydrogen transfer reagent was essential. Fluoboric acid (HBF₄) significantly improved the yield. Mild reaction conditions showed wide substrate scopes. In addition, the straightforward and efficient one-pot procotol, involved a multicomponent reaction of ethyl glyoxalate, primary amine and TCNHPI active ester occurred smoothly. This scheme provides a new method for the synthesis of α-alkylated unnatural amino acid derivatives.

Key words: photocatalysis, N-aromatic glyoxylimines, decarboxylation, one-pot, unnatural amino acid derivatives

Cite this article

Yongling Wang, Tiexin Zhang, Xuming Zhang, Hanyang Sun, Jinyao Leng, Yaming Li. Synthesis of Unnatural Amino Acid Derivatives by Visible- Light-Catalyzed Decarboxylative Alkylation of N-Aromatic Glyoxylimines[J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4284-4293.

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Entry	Catalyst	Additive	Solvent	Yield^b/%
1	Ru(bpy)₃Cl₂	—	DCM	30
2	4CzIPN	—	DCM	16
3	Eosin Y	—	DCM	<10
4	Ir(ppy)₃	—	DCM	41
5^c	Ir(ppy)₃	—	DCM	42
6^d	Ir(ppy)₃	—	DCM	n.d.^e
7f	Ir(ppy)₃	—	DCM	n.d.
8^g	Ir(ppy)₃	—	DCM	27
9	Ir(ppy)₃	K₂CO₃	DCM	61
10	Ir(ppy)₃	(NH₄)₂CO₃	DCM	60
11	Ir(ppy)₃	PhCOOH	DCM	56
12	Ir(ppy)₃	CF₃COOH	DCM	44
13	Ir(ppy)₃	ⁱPr₂NEt•HBF₄	DCM	76
14^h	Ir(ppy)₃	ⁱPr₂NEt•HBF₄	DCM	55
15ⁱ	Ir(ppy)₃	ⁱPr₂NEt•HBF₄	DCM	61
16^j	Ir(ppy)₃	ⁱPr₂NEt•HBF₄	DCM	75
17^k	Ir(ppy)₃	ⁱPr₂NEt•HBF₄	DCM	73
18	Ir(ppy)₃	ⁱPr₂NEt•HBF₄	DMF	78
19	Ir(ppy)₃	ⁱPr₂NEt•HBF₄	MeCN	52
20	Ir(ppy)₃	ⁱPr₂NEt•HBF₄	DMSO	85
21^l	Ir(ppy)₃	ⁱPr₂NEt•HBF₄	DMSO	83
22	—	ⁱPr₂NEt•HBF₄	DMSO	32

Entry	Catalyst	Additive	Solvent	Yield^b/%
1	Ru(bpy)₃Cl₂	—	DCM	30
2	4CzIPN	—	DCM	16
3	Eosin Y	—	DCM	<10
4	Ir(ppy)₃	—	DCM	41
5^c	Ir(ppy)₃	—	DCM	42
6^d	Ir(ppy)₃	—	DCM	n.d.^e
7f	Ir(ppy)₃	—	DCM	n.d.
8^g	Ir(ppy)₃	—	DCM	27
9	Ir(ppy)₃	K₂CO₃	DCM	61
10	Ir(ppy)₃	(NH₄)₂CO₃	DCM	60
11	Ir(ppy)₃	PhCOOH	DCM	56
12	Ir(ppy)₃	CF₃COOH	DCM	44
13	Ir(ppy)₃	ⁱPr₂NEt•HBF₄	DCM	76
14^h	Ir(ppy)₃	ⁱPr₂NEt•HBF₄	DCM	55
15ⁱ	Ir(ppy)₃	ⁱPr₂NEt•HBF₄	DCM	61
16^j	Ir(ppy)₃	ⁱPr₂NEt•HBF₄	DCM	75
17^k	Ir(ppy)₃	ⁱPr₂NEt•HBF₄	DCM	73
18	Ir(ppy)₃	ⁱPr₂NEt•HBF₄	DMF	78
19	Ir(ppy)₃	ⁱPr₂NEt•HBF₄	MeCN	52
20	Ir(ppy)₃	ⁱPr₂NEt•HBF₄	DMSO	85
21^l	Ir(ppy)₃	ⁱPr₂NEt•HBF₄	DMSO	83
22	—	ⁱPr₂NEt•HBF₄	DMSO	32

可见光催化N-芳基乙醛酸亚胺脱羧烷基化合成非天然氨基酸衍生物