4.7 Article

From Mono-Triazolium Salt to Bis-Triazolium Salt: Improvement of the Asymmetric Intermolecular Benzoin Condensation

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 350, Issue 16, Pages 2645-2651

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200800371

Keywords

asymmetric berizoin condensation; chiral bis-bicyclic triazolium salts; N-heterocyclic carbene; organocatalysis

Funding

  1. National Natural Science Foundation of China [20572074, 20772086]
  2. Program for New Century Excellent Talents in University [NCET-04-0881]
  3. Outstanding Young Scientist Award of Sichuan Province

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A solution to the long-standing challenge of developing a highly effective method for the enantioselective intermolecular benzoin condensation of aromatic aldehydes is described. The chiral bis-bicyclic triazolium salt - 1,3-bis{(S)-5-benzyl-6,8-dihydro-5H-[1,4]oxazino[2,1-c][1,2,4]triazol-2-ium-2-yl}benzene dichloride [(S)-5a-1] is currently the most efficient precatalyst for the asymmetric variant of the berizoin condensation.

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