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Enantio‐ and Diastereoselective Nucleophilic Addition of N ‐ tert ‐Butylhydrazones to Isoquinolinium Ions through Anion‐Binding Catalysis
Author(s) -
Matador Esteban,
IglesiasSigüenza Javier,
Monge David,
Merino Pedro,
Fernández Rosario,
Lassaletta José M.
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202012861
Subject(s) - chemistry , stereocenter , catalysis , carbanion , reagent , nucleophile , hydrazone , nucleophilic addition , thiourea , ion , combinatorial chemistry , medicinal chemistry , enantioselective synthesis , organic chemistry
A highly enantio‐ and diastereoselective thiourea‐catalyzed dearomatization of isoquinolines employing N‐ tert ‐butylhydrazones as neutral α‐azo carbanions and masked acyl anion equivalents has been developed. Experimental and computational data supports the generation of highly ordered complexes wherein the chloride behaves as a template for the catalyst, the hydrazone reagent, and the isoquinolinium cation, providing excellent stereocontrol in the formation of two contiguous stereogenic centers. The ensuing selective and high‐yielding transformations provide appealing dihydroisoquinoline derivatives.