Journal
CHEMICAL SCIENCE
Volume 11, Issue 28, Pages 7444-7450Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0sc02878a
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Funding
- European Union's Horizon 2020 Research and Innovation Program under the Marie Sklodowska-Curie grant [751281-H2020-MSCA-IF-2016]
- Honjo International Scholarship Foundation
- Netherlands Organization for Scientific Research (NWO)
- Leverhulme Trust [RPG-2017-069]
- EU commission [PIEF-GA-2013-627232]
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The construction of enantioenriched azabicyclo[3.3.1]nonan-6-one heterocyclesviaan enantioselective desymmetrization of allene-linked cyclohexanones, enabled through a dual catalytic system, that provides synchronous activation of the cyclohexanone with a chiral prolinamide and the allene with a copper(i) co-catalyst to deliver the stereodefined bicyclic core, is described. Successful application to oxygen analogues was also achieved, thereby providing a new enantioselective synthetic entry to architecturally complex bicyclic ethereal frameworks. The mechanistic pathway and the origin of enantio- and diastereoselectivities has been uncovered using density functional theory (DFT) calculations.
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