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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Modular Synthesis of Optically Active Tröger's Base Analogues
Takuya Kamiyama1, Merve Sinem Özer2, Elisabeth Otth1
1Department of Chemistry and Applied Biosciences, Swiss Federal Institute of Technology, ETH Zurich, HCI H230, Wolfgang-Pauli-Strasse 10, 8093 Zürich (Switzerland), Fax: (+41) 44-6321310.
Enantioselective catalysis and enzymatic resolution enable scalable synthesis of enantiopure Tröger's base derivatives. This provides valuable N-stereogenic building blocks for diverse chemical modifications.
Area of Science:
- Organic Chemistry
- Asymmetric Synthesis
- Catalysis
Background:
- Tröger's bases are important N-stereogenic compounds.
- Previous synthetic methods lacked enantioselectivity or scalability.
Purpose of the Study:
- To develop an enantioselective catalytic method for Tröger's base synthesis.
- To establish a scalable and flexible route to enantiopure Tröger's base derivatives.
Main Methods:
- Application of enantioselective catalysis for direct synthesis.
- Enzymatic kinetic resolution of racemic Tröger's bases.
- Subsequent chemical modifications of resolved bases.
Main Results:
- Achieved excellent enantiomeric purity in Tröger's base derivatives.
- Demonstrated easy scalability of the synthetic approach.
- Confirmed stability of stereogenic information during further modifications.
Conclusions:
- A practical and flexible route to enantiopure Tröger's base analogues is established.
- Enantioselective catalysis and enzymatic resolution are key tools for accessing these valuable building blocks.
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