Easy Access to Polyfunctionalized Chiral Decalins.
Hugo Santalla1,2, Zoila Gándara1,2, Uxía Gómez-Bouzó1,2
1Departamento de Química Orgánica, Facultad de Química and Instituto de Investigación Sanitaria Galicia Sur (IISGS), University of Vigo, Campus Marcosende, 36310 Vigo, Spain.
ACS Omega
|October 19, 2020
Summary
Researchers discovered a novel dyotropic reaction to transform hydrindanes into polyfunctionalized chiral decalins. This provides a new synthetic route for valuable organic compounds and potential applications in catalysis and drug discovery.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Chiral decalins are important structural motifs in natural products and pharmaceuticals.
- Access to polyfunctionalized chiral decalins is often challenging.
- Dyotropic reactions offer unique pathways for molecular rearrangement.
Purpose of the Study:
- To report a novel ring expansion reaction converting hydrindanes to decalins.
- To demonstrate the utility of this reaction for synthesizing polyfunctionalized chiral decalins.
- To highlight potential applications of these decalins in synthesis and catalysis.
Main Methods:
- A novel dyotropic rearrangement reaction was employed.
- The reaction involves a mesylate group facilitating ring expansion.
- Synthesis of polyfunctionalized chiral decalins from hydrindane precursors was achieved.
Main Results:
- An unexpected ring expansion of hydrindanes into decalins was observed.
- The reaction proceeds via an unprecedented dyotropic mechanism.
- Easy access to polyfunctionalized chiral decalins was established.
Conclusions:
- The developed dyotropic reaction provides efficient access to valuable polyfunctionalized chiral decalins.
- These decalins serve as versatile building blocks for synthesizing thia analogues of natural compounds and modified Vitamin D analogues.
- The findings hold potential for applications in asymmetric catalysis, particularly with chiral sulfoxide ligands.
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