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Diastereomeric Atropisomers from a Chiral Diyne by Cobalt(I)‐Catalyzed Cyclotrimerization
Author(s) -
Fischer Fabian,
Jungk Phillip,
Weding Nico,
Spannenberg Anke,
Ott Holger,
Hapke Marko
Publication year - 2012
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.201200402
Subject(s) - atropisomer , diastereomer , chemistry , cycloaddition , circular dichroism , catalysis , stereochemistry , organic chemistry
The reaction of new, chiral, proline‐based naphthyl diynes with different nitriles through a key [2+2+2] cycloaddition reaction step catalyzed by Co I –olefin complexes under thermal and photochemical conditions gave diastereomeric atropisomers in good yield and nearly 1:1 ratios. Facile chromatographic separation of the naphthyl tetrahydroisoquinolines gave access to both pure and stable diastereomeric atropisomers. The deprotection and direct functionalization of the methyl‐ or methoxymethyl‐protected 2‐naphthyl position of the atropisomers were investigated. The configuration of the formed atropisomers was assigned from results of X‐ray studies and circular dichroism spectroscopy.