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Enantio- and diastereoselective conjugate borylation/Mannich cyclization
Egor M Larin1, Joachim Loup1, Iuliia Polishchuk1
1Davenport Laboratories, Department of Chemistry, University of Toronto 80 St. George St. Toronto Ontario M5S 3H6 Canada mark.lautens@utoronto.ca.
This study introduces a novel copper-catalyzed reaction for stereoselective conjugate borylation and Mannich cyclization. The method efficiently creates complex borylated tetrahydroquinolines with multiple stereocenters from simple Michael acceptors.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
- Catalysis
Background:
- Enolate intermediates from conjugate borylation of α,β-unsaturated carbonyl systems are valuable but underutilized.
- Michael acceptors are ubiquitous in organic synthesis, offering potential for complex scaffold generation.
Purpose of the Study:
- To develop a mild and stereoselective method for synthesizing borylated tetrahydroquinoline scaffolds.
- To explore the synthetic utility of these complex heterocyclic compounds.
Main Methods:
- Copper-catalyzed conjugate borylation reaction.
- Tandem Mannich cyclization.
- Utilized a range of Michael acceptors.
Main Results:
- Achieved a mild and stereoselective copper-catalyzed conjugate borylation/Mannich cyclization.
- Successfully generated versatile borylated tetrahydroquinoline scaffolds.
- Demonstrated the formation of three contiguous stereocenters.
- Explored derivatization studies to showcase synthetic potential.
Conclusions:
- The developed strategy provides efficient access to valuable borylated tetrahydroquinolines.
- This method broadens the synthetic utility of conjugate borylation and Mannich cyclization.
- The generated scaffolds offer significant potential for further chemical exploration and application.
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