4.7 Article

Asymmetric Reduction of tert-Butanesulfinyl Ketimines by N-Heterocyclic Carbene Boranes

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 80, Issue 22, Pages 11441-11446

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b02084

Keywords

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Funding

  1. Shanghai Municipal Education Commission [14ZZ159]
  2. Scientific Research Foundation for the Returned Overseas Chinese Scholars
  3. State Education Ministry (SRF for ROCS, SEM)
  4. Special Scientific Foundation for Outstanding Young Teachers in Shanghai Higher Education Institutions [ZZGJD13020]
  5. Start-up Funding of Shanghai University of Engineering Science [2013-24]
  6. students Innovation Program in Shanghai University of Engineering Science [14KY0413]

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N-heterocyclic carbene borane (NHC-borane) baled on a triazole core is demonstrated for the first time to be efficient for reduction of a variety of tert-butanesulfinyl ketimines. Up to 95% yield and up to >99% diastereomeric excess were achieved. NHC-borane exhibited excellent activities that are more efficient than or comparable to commonly used reductive reagents such as NaBH4, NaBH3CN, L-selectride, Ru catalyst, or BH3-THF.

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