4.8 Article

Merging photoredox catalysis with organocatalysis: The direct asymmetric alkylation of aldehydes

Journal

SCIENCE
Volume 322, Issue 5898, Pages 77-80

Publisher

AMER ASSOC ADVANCEMENT SCIENCE
DOI: 10.1126/science.1161976

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Funding

  1. NIH General Medical Sciences [R01 GM078201-01-01]
  2. Merck
  3. Amgen
  4. Bristol-Myers Squibb
  5. NIH National Service Research Award [F32GM076816]

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Photoredox catalysis and organocatalysis represent two powerful fields of molecule activation that have found widespread application in the areas of inorganic and organic chemistry, respectively. We merged these two catalysis fields to solve problems in asymmetric chemical synthesis. Specifically, the enantioselective intermolecular alpha-alkylation of aldehydes has been accomplished using an interwoven activation pathway that combines both the photoredox catalyst Ru(bpy)(3)Cl-2 (where bpy is 2,2 '-bipyridine) and an imidazolidinone organocatalyst. This broadly applicable, yet previously elusive, alkylation reaction is now highly enantioselective and operationally trivial.

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