Journal
CHEMICAL SCIENCE
Volume 11, Issue 22, Pages 5716-5723Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0sc02421j
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Funding
- Natural Science and Engineering Research Council (NSERC)
- University of Toronto (U of T)
- Alphora/Eurofins Scientific
- Kennarshore Inc.
- NSERC
- Swiss National Science Foundation (SNSF) [P2SKP2_187649]
- Walter C. Sumner Memorial Fellowship, Province of Ontario (OGS)
- Swiss National Science Foundation (SNF) [P2SKP2_187649] Funding Source: Swiss National Science Foundation (SNF)
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Strategies to capitalize on enolate intermediates generated from stereoselective conjugate borylation to alpha,beta-unsaturated carbonyl systems are surprisingly rare despite the ubiquity of Michael acceptors, and the potential to generate valuable scaffolds bearing multiple stereocenters. Herein, we report a mild and stereoselective copper-catalyzed conjugate borylation/Mannich cyclization reaction. This strategy is feasible with a broad range of Michael acceptors, and can be leveraged to generate versatile borylated tetrahydroquinoline scaffolds bearing three contiguous stereocenters. The synthetic potential of these complex heterocycles has been explored through a series of derivatization studies.
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