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Latent Nucleophiles in Lewis Base Catalyzed Enantioselective N ‐Allylations of N‐Heterocycles
Author(s) -
Zi You,
Lange Markus,
Schultz Constanze,
Vilotijevic Ivan
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201903392
Subject(s) - nucleophile , chemistry , cinchona , enantioselective synthesis , lewis acids and bases , catalysis , allylic rearrangement , substitution reaction , silylation , organic chemistry , combinatorial chemistry , organocatalysis , medicinal chemistry
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.