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CO Versus CC Bond Cleavage: Selectivity Control in Lewis Acid Catalyzed Chemodivergent Cycloadditions of Aryl Oxiranyldicarboxylates with Aldehydes, and Theoretical Rationalizations of Reaction Pathways
Author(s) -
Chen Zuliang,
Tian Ziqi,
Zhang Jieming,
Ma Jing,
Zhang Junliang
Publication year - 2012
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.201201453
Subject(s) - lewis acids and bases , aryl , chemistry , bond cleavage , catalysis , cleavage (geology) , selectivity , medicinal chemistry , lewis acid catalysis , stereochemistry , organic chemistry , materials science , alkyl , fracture (geology) , composite material
A clean break : Lewis acid catalyzed chemodivergent [3+2] cycloadditions of aryl oxiranyldicarboxylates with aldehydes are revealed, in which the CC or CO bond cleavage of oxiranes can be controlled by the use of Ni(ClO 4 ) 2 or Sn(OTf) 2 catalysts (see scheme). Possible reaction pathways for these transformations are demonstrated by theoretical calculations.