Taming Silylium Ions for Synthesis: N-Heterocycle Synthesis via Stereoselective C-C Bond Formation

Silylium ions (formally [R3Si](+)) have long been the subject of investigations and significant debate in both theoretical and experimental chemistry, but few catalytic, synthetic applications have been reported due to the exceptionally high reactivity and Lewis acidity of these elusive species. Res...

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Bibliographic Details
Published inSynlett Vol. 28; no. 18; pp. 2429 - 2434
Main Authors Moyer, Brandon S., Gagne, Michel R.
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 13.11.2017
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Lewis acid
STABILIZED SILICON CATIONS
BRONSTED ACID
N-heterocycle
ACTIVATION
DIELS-ALDER REACTIONS
polycyclic scaffold
HYDRODEFLUORINATION
silylium catalysis
Hosomi-Sakurai allylation
R3SI
Si-X reagent
silylium ion
CHEMISTRY
BETA-SILYL
LEWIS-ACIDS
Prins cyclization
MUKAIYAMA ALDOL
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Summary:Silylium ions (formally [R3Si](+)) have long been the subject of investigations and significant debate in both theoretical and experimental chemistry, but few catalytic, synthetic applications have been reported due to the exceptionally high reactivity and Lewis acidity of these elusive species. Results to be discussed include the application of easily accessible silylium ion catalysts to the stereoselective synthesis of various N-heterocyclic pyrrolidine and piperidine scaffolds. The tested substrates are derived from the chiral pool and can be obtained in three high-yielding steps from amino alcohols; subsequent stereoselective silylium ion catalyzed Prins cyclization and trapping with R3Si-Nu nucleophiles (e.g., Nu = H, allyl, azide, and enol ethers) results in novel nitrogen-containing polycyclic scaffolds with potential medicinal chemistry applications.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0036-1590967