Dihydropyridine Derivative Forming a Leaving Group for Photoredox Reactions

3,5-Bis(ethoxycarbonyl)-2,6-dimethyl-1,4-dihydropyridine-4-carboxylic acid (1) is known to form an eliminating group for photoredox reactions when condensed with an alcohol or an amine. For example, the C-glycosylation reaction proceeds when the intermediate derived from 1 and the protected ribose is treated with a (hetero)aryl bromide in the presence of a nickel catalyst and a photoredox catalyst under photoradiation conditions.¹⁾ The advantage of this reaction is that 1-(hetero)aryl-β-ribose is generated in high stereoselectivity. Furthermore, a carbamoyl group can be introduced to aryl bromides by adding the amide derived from 1 under similar conditions as above.²⁾ This reaction is anticipated to be used in medicinal chemistry, as it can also be applied to complicated substances like bioactive compounds. Additionally, it is reported that 1 can be utilized in electrolytic reactions,³⁾ so that the use of 1 in a wide range of research is expected.

References

• 1) Diastereoselective Synthesis of Aryl C-Glycosides from Glycosyl Esters via C-O Bond Homolysis
  • Y. Wei, B. Ben-zvi, T. Diao, Angew. Chem. Int. Ed. 2021, 60, 9433.
• 2) Amide Synthesis by Nickel/Photoredox-Catalyzed Direct Carbamoylation of (Hetero)Aryl Bromides
  • N. Alandini, L. Buzzetti, G. Favi, T. Schulte, L. Candish, K. D. Collins, P. Melchiorre, Angew. Chem. Int. Ed. 2020, 59, 5248.
• 3) Ynonylation of Acyl Radicals by Electroinduced Homolysis of 4-Acyl-1,4-dihydropyridines
  • X. Luo, P. Wang, Org. Lett. 2021, 23, 4960.

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