6533b835fe1ef96bd129ffaa
RESEARCH PRODUCT
Tandem gold self-relay catalysis for the synthesis of 2,3-dihydropyridin-4(1 H)-ones: combination of σ and π Lewis acid properties of gold salts.
Javier MiróSantos FusteroCarlos Del PozoMaría Sánchez-rosellósubject
Nucleophilic additionChemistryOrganic ChemistryGeneral ChemistryTriple bondCombinatorial chemistryCatalysisCatalysischemistry.chemical_compoundIntramolecular forceAmideGold saltsmedicineOrganic chemistryLewis acids and basesTrifluoromethanesulfonatemedicine.drugdescription
The dual ability of gold salts to act as π- and σ Lewis acids has been exploited in a tandem self-relay catalysis. Thus, triphenylphosphanegold(I) triflate mediated the intramolecular carbonyl addition of the amide functionality of homoprogargyl amides to a triple bond. The formation of a σ complex of the gold salt with the intermediate oxazine promoted a nucleophilic addition followed by a Petasis-Ferrier rearrangement. This tandem protocol, catalyzed by the same gold salt under the same reaction conditions, gave rise to the efficient synthesis of 2,3-dihydropyridin-4-(1 H)-ones, which contain a cyclic quaternary α-amino acid unit. The asymmetric version was performed by generating the starting materials from the corresponding sulfinylimines.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2014-04-30 | Chemistry (Weinheim an der Bergstrasse, Germany) |