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Asymmetric Catalytic Oxidative Cleavage of Polycyclic Systems: The Synthesis of Atropisomeric Diazonanes and Diazecanes
Author(s) -
Jones Alan M.,
Liu Gu,
Lorion Magali M.,
Patterson Stephen,
Lebl Tomas,
Slawin Alexandra M. Z.,
Westwood Nicholas J.
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201003188
Subject(s) - oxidative cleavage , ruthenium , cleavage (geology) , atropisomer , catalysis , chemistry , oxidative phosphorylation , bond cleavage , stereochemistry , combinatorial chemistry , organic chemistry , materials science , biochemistry , fracture (geology) , composite material
Oxidative cleavage of internal double bonds in polycyclic systems can give access to compounds containing medium‐ to large‐sized rings. In this example, the nine‐ and ten‐membered ring containing compounds that resulted from the m CPBA‐mediated ( m CPBA= meta ‐chloroperoxybenzoic acid) oxidative cleavage reaction were shown to exhibit atropisomerism. The reaction of the polycyclic system with catalytic amounts of ruthenium tetraoxide followed by diol cleavage achieved the same synthetic goal. Use of the Nishiyama–Beller ruthenium‐based catalysts enabled the synthesis of optically‐enriched samples, providing the first example of an atropselective oxidative cleavage reaction.