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Transannular macrocyclization via intramolecular B-alkyl Suzuki reaction
1Department of Bioorganic Chemistry, Sloan-Kettering Institute for Cancer Research, New York, New York 10021, USA.
Organic Letters
|September 16, 2000
Summary
This study introduces a new method for creating macrocycles using intramolecular B-alkyl Suzuki reactions. This approach offers precise control over olefin geometry, complementing existing ring-closing metathesis techniques.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Macrocyclization is crucial for synthesizing complex molecules.
- Existing methods like ring-closing metathesis (RCM) have limitations in controlling olefin geometry.
Purpose of the Study:
- To develop a novel method for transannular macrocyclization.
- To achieve high control over olefin geometry during macrocycle formation.
Main Methods:
- Regioselective terminal olefin hydroboration using 9-Borabicyclo[3.3.1]nonane (9-BBN).
- Palladium(0)-catalyzed intramolecular Suzuki coupling reaction.
- High dilution conditions and use of bases like Thallium(I) ethoxide (TlOEt).
Main Results:
- Successful synthesis of macrocycles via intramolecular B-alkyl Suzuki reactions.
- Demonstrated high control over olefin geometry, yielding isomerically pure E or Z vinyl iodides.
- The method is complementary to RCM.
Conclusions:
- Intramolecular B-alkyl Suzuki reactions provide a powerful and controlled route to macrocycles.
- This method offers an advantage over RCM when precise olefin geometry is required.