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Asymmetric Counterion Pair Catalysis: An Enantioselective Brønsted Acid‐Catalyzed Protonation
Author(s) -
Rueping Magnus,
Theissmann Thomas,
Raja Sadiya,
Bats Jan W.
Publication year - 2008
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200800020
Subject(s) - chemistry , protonation , enantioselective synthesis , brønsted–lowry acid–base theory , stereocenter , cascade reaction , catalysis , cascade , hydride , organocatalysis , combinatorial chemistry , triflic acid , counterion , organic chemistry , ion , hydrogen , chromatography
A new asymmetric Brønsted acid‐catalyzed cascade reaction involving a 1,4‐addition, enantioselective protonation and 1,2‐addition has been developed. This organocatalytic cascade not only provides for the first time 3‐ and 2,3‐substituted tetrahydroquinolines and octahydroacridines in good yields with high dia‐ and enantioselectivities under mild reaction conditions but additionally represents the first example of a chiral Brønsted acid‐catalyzed protonation reaction in an organocatalytic domino reaction. Furthermore, the new Brønsted acid‐catalyzed hydride‐proton‐hydride transfer cascade can be applied to prepare new molecular scaffolds with up to three new stereocenters in an efficient one‐pot reaction sequence.