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Nucleophile Screening in Anion‐Binding Reissert‐Type Reactions of Quinolines with Chiral Tetrakis(triazole) Catalysts
Author(s) -
Duong QuiNhi,
Schifferer Lukas,
García Mancheño Olga
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900566
Subject(s) - nucleophile , chemistry , enantioselective synthesis , catalysis , quinoline , ketene , amide , combinatorial chemistry , triazole , organocatalysis , organic chemistry
A nucleophile screening for the organocatalyzed enantioselective Reissert‐type dearomatization of quinoline derivatives using chiral triazoles as anion‐binding catalysts was realized. Our recently reported helical tetrakis(triazole) catalysts (TetraTri) have proven to be highly active in this type of reactions, however the methods were limited to nucleophiles with a N value of 10 according to the Mayr's nucleophilicity scale. In this study, different carbon‐nucleophiles of varied nucleophilicity N ‐values were explored, allowing the identification of potential novel reaction partners with N >5 such as ketene thioacetals. Thus, a number of chiral 1,2‐dihydroisoquinoline‐thioesters with an enantioselectivity up to 92:8 er . were synthetized, which could easily be transformed into a more valuable amide derivative.