Abstract
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 α-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.
Keywords
Enantioselective synthesisOrganocatalysisAlkylationChemistryPhotoredox catalysisCatalysisIntermolecular forceOrganic synthesisCombinatorial chemistrySynergistic catalysisBipyridineOrganic chemistryMoleculePhotocatalysis
MeSH Terms
22'-DipyridylAldehydesAlkylationCatalysisCoordination ComplexesElectronsLightLuminescenceOxidation-ReductionPhotonsStereoisomerism
Affiliated Institutions
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Publication Info
- Year
- 2008
- Type
- article
- Volume
- 322
- Issue
- 5898
- Pages
- 77-80
- Citations
- 2362
- Access
- Closed
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Cite This
David A. Nicewicz,
David W. C. MacMillan
(2008).
Merging Photoredox Catalysis with Organocatalysis: The Direct Asymmetric Alkylation of Aldehydes.
Science
, 322
(5898)
, 77-80.
https://doi.org/10.1126/science.1161976
Identifiers
- DOI
- 10.1126/science.1161976
- PMID
- 18772399
- PMCID
- PMC2723798