Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 85, Issue 2, Pages 1259-1269Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b02819
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Funding
- Carl-Zeiss Foundation
- Friedrich Schiller University Jena
- State of Thuringia
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Pyrrolizidine alkaloids and their derivatives often feature interesting biological activities. A class of substituted 2,3-dihydro-1H-pyrrolizin-1-one derivatives has been explored as a potential treatment for Alzheimer's disease, but enantioselective synthesis of these molecules is still elusive. We report that enantioselective N-allylation of N-silyl pyrrole latent nucleophiles with allylic fluorides followed by hydrogenation and diastereoselective Friedel-Crafts cyclization constitute an efficient synthetic route to access enantioenriched substituted 2,3-dihydro-1H-pyrrolizin-1-ones.
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