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A Simple and Broadly Applicable C−N Bond Forming Dearomatization Protocol Enabled by Bifunctional Amino Reagents
Author(s) -
Ma Xiaofeng,
Farndon Joshua J.,
Young Tom A.,
Fey Natalie,
Bower John F.
Publication year - 2017
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.201708176
Subject(s) - bifunctional , reagent , chemistry , electrophile , nucleophile , combinatorial chemistry , scope (computer science) , organic chemistry , stereochemistry , computer science , catalysis , programming language
A C−N bond forming dearomatization protocol with broad scope is outlined. Specifically, bifunctional amino reagents are used for sequential nucleophilic and electrophilic C−N bond formations, with the latter effecting the key dearomatization step. Using this approach, γ‐arylated alcohols are converted to a wide range of differentially protected spirocyclic pyrrolidines in just two or three steps.