Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 137, Issue 30, Pages 9539-9542Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.5b05786
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Funding
- Ministry of Education, Culture, Sports, Science and Technology (Japan) [25E07B212, 22750088, 24510112, 24106713]
- Advanced Catalytic Transformation Program for Carbon Utilization (ACT-C) from Japan Science and Technology Agency (JST)
- Grants-in-Aid for Scientific Research [24510112, 22750088, 24106713] Funding Source: KAKEN
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Tsuji-Trost-type asymmetric allylation of carboxylic acids has been realized by using a cationic CpRu complex with an axially chiral picolinic acid-type ligand (C1-Naph-PyCOOH: naph = naphthyl, py = pyridine). The Carboxylic acid and allylic alcohol intramolecularly condense by the liberation of water Without stoichiometric activation of either nucleophile or electrophile part, thereby attaining high atom- and step-economy, and low E factor. This success can be ascribed to the higher reactivity of allylic alcohols as compared with the allyl ester products in soft Ru/hard Brunstead acid combined catalysis, which can function under slightly acidic conditions unlike the traditional Pd-catalyzed system. Detailed analysis of the stereochemical outcome of the reaction using an enantiomerically enriched D-labeled substrate provides an intriguing view of enantioselection.
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