Latent Nucleophiles in Lewis Base Catalyzed Enantioselective N-Allylations of N-Heterocycles

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.

Keywords: Lewis base catalysis; allylation; latent nucleophiles; nitrogen heterocycles; nucleophilic substitution.