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Synergistic Catalysis: Highly Enantioselective Cascade Reaction for the Synthesis of Dihydroacridines
Author(s) -
Meninno Sara,
Meazza Marta,
Yang Jung Woon,
Tejero Tomas,
Merino Pedro,
Rios Ramon
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201901498
Subject(s) - enantioselective synthesis , catalysis , cascade , aldol reaction , chemistry , stereoselectivity , iminium , lewis acids and bases , combinatorial chemistry , cascade reaction , organic chemistry , reaction conditions , organocatalysis , chromatography
The first stereoselective synthesis of dihydroacridines through synergistic catalysis, achieving the final target compounds with good to excellent yields and good to excellent enantioselectivities and diastereoselectivities, is reported. The synergistic approach consists in the activation of substituted quinolines with a Lewis acid catalyst that react in a cascade fashion with activated enals in the iminium form. Mechanistic calculations support a consecutive Michael–aldol reaction, followed by dehydration.