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Nucleophilic Addition of Organometallic Reagents to Cinchona Alkaloids: Simple Access to Diverse Architectures
Author(s) -
Hintermann Lukas,
Schmitz Marco,
Englert Ulli
Publication year - 2007
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.200701341
Subject(s) - nucleophile , aminal , reagent , chemistry , cinchona , nucleophilic addition , alkylation , organic chemistry , cinchona alkaloids , combinatorial chemistry , enantioselective synthesis , catalysis
Aminal pharm : Grignard reagents undergo a surprising nucleophilic aromatic addition reaction to cinchona alkaloids to stereoselectively produce cyclic aminals. Structurally diverse alkaloid derivatives with rigid cores that bear reactive functional groups (see examples) can be readily synthesized by this simple nucleophilic alkylation protocol.