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Modular Synthesis of Optically Active Tröger’s Base Analogues
Author(s) -
Kamiyama Takuya,
Özer Merve Sinem,
Otth Elisabeth,
Deska Jan,
Cvengroš Ján
Publication year - 2013
Publication title -
chempluschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.801
H-Index - 61
ISSN - 2192-6506
DOI - 10.1002/cplu.201300295
Subject(s) - enantiopure drug , stereocenter , kinetic resolution , enantioselective synthesis , combinatorial chemistry , yield (engineering) , enantiomeric excess , chemistry , enantiomer , catalysis , base (topology) , stereochemistry , organic chemistry , mathematics , materials science , mathematical analysis , metallurgy
For the first time, enantioselective catalysis was applied for the preparation of Tröger’s base derivatives affording N‐stereogenic building blocks not only in excellent enantiomeric purity but also in an easily scalable fashion. Enzymatic kinetic resolution proved efficient to yield functionalized Tröger’s bases, which can be subsequently modified by various chemical methods without any erosion of stereogenic information. In concert with a preparatively convenient protocol for the synthesis of the racemic substrates from commercially available anilines, a highly practicable and flexible route towards a wide range of enantiopure Tröger’s base analogues is provided.