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Structural diversity based on cyclopropane scaffolds
1Department of Chemistry and Biochemistry, University of Notre Dame, Indiana 46556-5670, USA. taylor.61@nd.edu
Organic Letters
|May 18, 2000
Summary
A new method efficiently converts homoallylic alcohols into pure cyclopropanes. This stereoselective synthesis is ideal for creating diverse molecular structures and libraries.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Cyclopropanes are valuable structural motifs in medicinal chemistry.
- Efficient and stereoselective synthesis of substituted cyclopropanes remains a challenge.
Purpose of the Study:
- To develop a practical and efficient method for synthesizing diastereomerically pure cyclopropanes.
- To enable the preparation of diverse cis- and trans-disubstituted and 1,2,3-trisubstituted cyclopropanes.
Main Methods:
- Stereoselective conversion of homoallylic alcohols.
- A sequence amenable to solid-phase synthesis.
Main Results:
- Achieved diastereomerically pure cis- and trans-disubstituted cyclopropanes.
- Achieved diastereomerically pure 1,2,3-trisubstituted cyclopropanes.
- Demonstrated the route's suitability for combinatorial library generation.
Conclusions:
- A practical and efficient stereoselective route to diverse cyclopropanes has been established.
- The developed method is ideal for solid-phase synthesis and combinatorial library generation.