Enantioselective Synthesis of Pyrrolizin-1-ones via Lewis Base Catalyzed N‑Allylation of N‑Silyl Pyrrole Latent Nucleophiles

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...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 85; no. 2; pp. 1259 - 1269
Main Authors Lange, Markus, Zi, You, Vilotijevic, Ivan
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 17.01.2020
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
INHIBITION
ALKYLATION
POCHONICINE
DERIVATIVES
LICOFELONE
FLUORIDES
TRANSFORMATIONS
INDOLES
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Summary: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.
Bibliography:ObjectType-Article-1
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b02819