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Protected indanones by a Heck-aldol annulation reaction
Anna Bengtson1, Mats Larhed, Anders Hallberg
1Department of Organic Pharmaceutical Chemistry, Uppsala University, BMC, Box-574, SE-751 23 Uppsala, Sweden.
The Journal of Organic Chemistry
|August 3, 2002
Summary
A novel tandem reaction efficiently synthesizes monoprotected 3-hydroxyindan-1-ones using salicylaldehyde triflates and vinyl ether. This one-pot palladium-catalyzed annulation forms two new ring systems.
Area of Science:
- Organic Chemistry
- Synthetic Methodology
- Catalysis
Background:
- Indanone derivatives are important structural motifs in medicinal chemistry.
- Efficient synthetic routes to functionalized indanones are highly sought after.
- Palladium-catalyzed reactions offer powerful tools for C-C bond formation.
Purpose of the Study:
- To develop a new one-pot tandem reaction for the synthesis of monoprotected 3-hydroxyindan-1-ones.
- To explore the utility of salicylaldehyde triflates in annulation reactions.
- To investigate the formation of novel bicyclic ring systems.
Main Methods:
- A tandem annulation reaction was employed.
- Salicylaldehyde triflates and 2-hydroxyethyl vinyl ether were used as starting materials.
- A palladium bidentate catalyst facilitated the reaction.
Main Results:
- Monoprotected 3-hydroxyindan-1-ones were prepared in moderate to good yields.
- The reaction proceeded as a one-pot process.
- Two new ring systems were successfully formed.
Conclusions:
- A new, efficient tandem annulation reaction has been established.
- This method provides access to valuable indanone scaffolds.
- The reaction offers a streamlined approach to complex ring systems.