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Resolution of [4]Heterohelicenium Dyes with Unprecedented Pummerer‐like Chemistry
Author(s) -
Laleu Benoît,
Mobian Pierre,
Herse Christelle,
Laursen Bo W.,
Hopfgartner Gérard,
Bernardinelli Gérald,
Lacour Jérôme
Publication year - 2005
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.200462321
Subject(s) - enantiopure drug , diastereomer , sulfoxide , chemistry , pummerer rearrangement , resolution (logic) , fragmentation (computing) , organic chemistry , enantioselective synthesis , computer science , artificial intelligence , acetic anhydride , catalysis , operating system
Addition of an enantiopure sulfoxide auxiliary is the key to the resolution of highly stable [4]helicenium dyes. This transformation allows a facile chromatographic separation of the diastereomers (the structure of one such diastereomer is shown; S yellow, O red, N blue). Then an unprecedented Pummerer‐like CC bond fragmentation takes place to release the enantiopure cations.