4.6 Article

Probing the evolution of an Ar-BINMOL-derived salen-Co(III) complex for asymmetric Henry reactions of aromatic aldehydes: salan-Cu(II) versus salen-Co(III) catalysis

Journal

RSC ADVANCES
Volume 4, Issue 71, Pages 37859-37867

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c4ra06056c

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Funding

  1. National Natural Science Foundation of China (NSFC) [21173064, 51203037]
  2. Zhejiang Provincial Natural Science Foundation of China [LR14B030001]
  3. Program for Excellent Young Teachers in Hangzhou Normal University (HNUEYT) [JTAS 2011-01-014]

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A new type of chiral salen-Co catalyst that features aromatic p-walls and an active Co(III) center has been developed for enantioselective Henry/nitroaldol reactions on the basis of salen-Cu catalysis. The asymmetric Henry reaction of aromatic aldehydes and nitromethane catalyzed by an Ar-BINMOL derived salen-Co(III) complex was achieved with high yields (up to 93%) and excellent enantioselectivities (up to 98% ee). And more interestingly, it was supposed that either salan-Cu(II) or salen-Co(III) complex catalyzed Henry reaction was an ideal model reaction for providing direct evidence of noncovalent interaction due to the distinguishable ortho-substituted aromatic aldehydes from meta-or parasubstituted benzaldehydes in terms of enantioselectivities and yields.

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