4.8 Article

Enantioselective Organocatalytic Michael Addition of Nitroalkanes and Other Nucleophiles to β-Trifluoromethylated Acrylamides

Journal

ACS CATALYSIS
Volume 3, Issue 4, Pages 502-506

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/cs300806w

Keywords

trifluoromethyl; organocatalyst; Michael addition; fluorine; asymmetric

Funding

  1. National Basic Research Program of China [2012CB821600, 2010CB126103]
  2. Key Program of National Natural Science Foundation of China [21032006]
  3. National Natural Science Foundation of China [21172244/21172245/B020304]
  4. Agro-scientific Research in the Public Interest [201103007]
  5. National Key Technologies RD Program [2011BAE06B05]
  6. Shanghai Scientific Research Program [10XD1405200]
  7. Shanghai Pujiang program [11PJ1412200]

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An organocatalytic asymmetric Michael addition of nitroalkanes to trifluoromethylated acrylamides in good yields and with good to excellent diastereoselectivities and excellent enantioselectivities is described. The Michael adducts could be readily transformed into optically pure trifluoromethylated gamma-aminobutyric acid 7 in high yields without loss in enantioselectivities.

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