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A Highly Enantioselective Brønsted Acid Catalyzed Cascade Reaction: Organocatalytic Transfer Hydrogenation of Quinolines and their Application in the Synthesis of Alkaloids
Author(s) -
Rueping Magnus,
Antonchick Andrey P.,
Theissmann Thomas
Publication year - 2006
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.200600191
Subject(s) - catalysis , transfer hydrogenation , enantioselective synthesis , cascade , chemistry , brønsted–lowry acid–base theory , aryl , alkyl , combinatorial chemistry , organic chemistry , organocatalysis , ruthenium , chromatography
A categorical success : A Brønsted acid catalyzed cascade transfer hydrogenation provides direct access to 2‐aryl‐ and 2‐alkyl‐substituted tetrahydroquinolines with excellent enantioselectivities under mild conditions and using very low amounts of catalyst (see scheme). The best results were achieved with the binol phosphate catalyst, where Ar=9‐phenanthryl, used successfully in the Strecker reaction.