4.8 Article

Catalytic asymmetric hydroamination of unactivated internal olefins to aliphatic amines

Journal

SCIENCE
Volume 349, Issue 6243, Pages 62-66

Publisher

AMER ASSOC ADVANCEMENT SCIENCE
DOI: 10.1126/science.aab3753

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Funding

  1. National Institutes of Health [GM 58160]
  2. University of Pittsburgh
  3. National Science Foundation

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Catalytic assembly of enantiopure aliphatic amines from abundant and readily available precursors has long been recognized as a paramount challenge in synthetic chemistry. Here, we describe a mild and general copper-catalyzed hydroamination that effectively converts unactivated internal olefins-an important yet unexploited class of abundant feedstock chemicals-into highly enantioenriched a-branched amines (>= 96% enantiomeric excess) featuring two minimally differentiated aliphatic substituents. This method provides a powerful means to access a broad range of advanced, highly functionalized enantioenriched amines of interest in pharmaceutical research and other areas.

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