Work

Selective Synthesis of Tetrahydroisoquinoline and Piperidine Scaffolds by Oxidative Ring Opening/Ring Closing Protocols of Substituted Indenes and Cyclopentenes

Year: 2024

Type: article

Abstract: Novel tetrahydroisoquinoline and piperidine derivatives were selectively synthesized from substituted indenes or cyclopentenes. The process starts with an oxidative cleavage of the ring olefin bond, which gives reactive diformyl intermediates. By a ring-closing step using chiral (R) or (S) α-methylbenzylamine under a reductive amination protocol facilitated ring formation with ring expansion of the corresponding nitrogen-containing heterocycles. The stereocontrolled methodology enabled accurate control of the stereochemistry of the final products. Additionally, the synthesized amino acid derivatives possessing an aryl moiety in their structure may be relevant building blocks for foldamer chemistry.

Source: ChemistryOpen

DOI: 10.1002/open.202400475

Authors: Anas Semghouli, László Drahos, Jianlin Han, Loránd Kiss, Melinda Nonn

Institutions: Institute of Organic Chemistry, HUN-REN Research Centre for Natural Sciences, Nanjing Forestry University, Institute of Materials and Environmental Chemistry, Hungarian Academy of Sciences

Language: English

Topic: Synthesis and Biological Activity

Subfield: Cancer Research

Field: Biochemistry, Genetics and Molecular Biology

Domain: Life Sciences

Open Access status: gold

Estimated APC paid: $2,540