Applications of Hantzsch Esters in Organocatalytic Enantioselective Synthesis

Hantzsch esters (1,4-dihydropyridine dicarboxylates) have become, in this century, very versatile reagents for enantioselective organic transformations. They can act as hydride transfer agents to reduce, regioselectively, a variety of multiple bonds, e.g., C=C and C=N, under mild reaction conditions. They are excellent reagents for the dearomatization of heteroaromatic substances, and participate readily in cascade processes. In the last few years, they have also become useful reagents for photoredox reactions. They can participate as sacrificial electron and hydrogen donors and when 4-alkyl or 4-acyl-substituted, they can act as alkyl or acyl radical transfer agents. These last reactions may take place in the presence or absence of a photocatalyst. This review surveys the literature published in this area in the last five years. © 2023 by the authors.

Authors
Faisca Phillips A.M. , Pombeiro A.J.L.
Journal
Publisher
MDPI AG
Number of issue
2
Language
English
Status
Published
Number
419
Volume
13
Year
2023
Organizations
  • 1 Coordination Chemistry and Catalysis Group, Centro de Química Estrutural, Institute of Molecular Sciences, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais 1, Lisboa, 1049-001, Portugal
  • 2 Research Institute of Chemistry, Peoples’ Friendship University of Russia (RUDN University), Moscow, 117198, Russian Federation
Keywords
1,4-dihydropyridine dicarboxylates; alkylation; chiral phosphoric acid; dearomatization; electron donor-acceptor complexes; enantioselective catalysis; photoredox catalysis; radical transfer; reduction; transfer hydrogenation; transfer-alkylation
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