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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Pd-catalyzed borylative cyclisation of 1,7-enynes
Virtudes Pardo-Rodríguez1, Elena Buñuel, Daniel Collado-Sanz
1Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, Campus de Cantoblanco, 28049-Madrid, Spain.
This study introduces a new palladium-catalyzed reaction using 1,7-enynes and bis(pinacolato) diboron. The process efficiently synthesizes valuable six-membered cyclic homoallylic and allylic boronates.
Area of Science:
- Organic Chemistry
- Organometallic Chemistry
- Catalysis
Background:
- 1,7-enynes are versatile substrates in organic synthesis.
- Boronate esters are important synthetic intermediates.
- Palladium catalysis enables efficient C-C and C-B bond formation.
Purpose of the Study:
- To develop a novel synthetic route to cyclic boronates.
- To explore the reactivity of 1,7-enynes in palladium-catalyzed borylation.
- To synthesize six-membered carbo- and heterocycles containing boronate esters.
Main Methods:
- Reaction of various 1,7-enynes with bis(pinacolato) diboron.
- Palladium bis(trifluoroacetate) catalyzed cyclization and borylation.
- Formation of carbon-carbon (C-C) and carbon-boron (C-B) bonds.
Main Results:
- Successful synthesis of homoallylic and allylic boronates.
- Formation of six-membered carbo- and heterocycles.
- Efficient C-C and C-B bond construction via a cascade process.
Conclusions:
- The developed palladium-catalyzed reaction provides a facile method for synthesizing cyclic boronates.
- This methodology expands the utility of 1,7-enynes in organic synthesis.
- The resulting boronates are valuable building blocks for further chemical transformations.
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