Latent Nucleophiles in Lewis Base Catalyzed Enantioselective N-Allylations of N-Heterocycles
You Zi
Institute of Organic Chemistry and Macromolecular Chemistry, Friedrich Schiller University Jena, Humboldtstr. 10, 07743 Jena, Germany
Search for more papers by this authorMarkus Lange
Institute of Organic Chemistry and Macromolecular Chemistry, Friedrich Schiller University Jena, Humboldtstr. 10, 07743 Jena, Germany
Search for more papers by this authorConstanze Schultz
Institute of Organic Chemistry and Macromolecular Chemistry, Friedrich Schiller University Jena, Humboldtstr. 10, 07743 Jena, Germany
Search for more papers by this authorCorresponding Author
Prof. Dr. Ivan Vilotijevic
Institute of Organic Chemistry and Macromolecular Chemistry, Friedrich Schiller University Jena, Humboldtstr. 10, 07743 Jena, Germany
Search for more papers by this authorYou Zi
Institute of Organic Chemistry and Macromolecular Chemistry, Friedrich Schiller University Jena, Humboldtstr. 10, 07743 Jena, Germany
Search for more papers by this authorMarkus Lange
Institute of Organic Chemistry and Macromolecular Chemistry, Friedrich Schiller University Jena, Humboldtstr. 10, 07743 Jena, Germany
Search for more papers by this authorConstanze Schultz
Institute of Organic Chemistry and Macromolecular Chemistry, Friedrich Schiller University Jena, Humboldtstr. 10, 07743 Jena, Germany
Search for more papers by this authorCorresponding Author
Prof. Dr. Ivan Vilotijevic
Institute of Organic Chemistry and Macromolecular Chemistry, Friedrich Schiller University Jena, Humboldtstr. 10, 07743 Jena, Germany
Search for more papers by this authorGraphical Abstract
Double activation required: Latent nucleophiles enlarge substrate scopes and improve selectivities in Lewis base catalysis. N-Silyl pyrroles, indoles, and carbazoles serve as latent N-centered nucleophiles in highly selective enantioselective Lewis base catalyzed substitutions of allylic fluorides.
Abstract
Latent nucleophiles are compounds that are themselves not nucleophilic but can produce a strong nucleophile when activated. Such nucleophiles can expand the scope of Lewis base catalyzed reactions. As a proof of concept, we report that N-silyl pyrroles, indoles, and carbazoles serve as latent N-centered nucleophiles in substitution reactions of allylic fluorides catalyzed by Lewis bases. The reactions feature broad scopes for both reaction partners, excellent regioselectivities, and produce enantioenriched N-allyl pyrroles, indoles, and carbazoles when chiral cinchona alkaloid catalysts are used.
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