Biomaterial Database

Synthesis of α-Acyloxyketone Derivatives via the Platinum-Catalyzed Migration of Propargylic Esters. 2015

Chihiro Tsukano, and Sho Yamamoto, and Yoshiji Takemoto

Graduate School of Pharmaceutical Sciences, Kyoto University.

The synthesis of α-acyloxyketones via the migration of a propargylic ester followed by the intramolecular nucleophilic addition of the resulting allene was achieved using a cationic platinum catalyst. The optimized conditions for this transformation were determined to be 3 mol% of Pt(cod)Cl2, 3 mol% of AgNTf2, and 3 eq of water in toluene at 100 °C, and these conditions were successfully applied to the synthesis of a wide variety of α-aryl-α-acyloxyketones. The mechanism of this reaction was evaluated in detail based on the results of isotope labeling experiments using H2(18)O.

UI	MeSH Term	Description	Entries
D009944	Organoplatinum Compounds	Organic compounds which contain platinum as an integral part of the molecule.	Compounds, Organoplatinum
D010984	Platinum	A heavy, soft, whitish metal, resembling tin, with atomic number 78, atomic weight 195.084, symbol Pt. It is used in manufacturing equipment for laboratory and industrial use. It occurs as a black powder (platinum black) and as a spongy substance (spongy platinum) and may have been known in Pliny's time as "alutiae".	Platinum Black
D002384	Catalysis	The facilitation of a chemical reaction by material (catalyst) that is not consumed by the reaction.	Catalyses
D004952	Esters	Compounds derived from organic or inorganic acids in which at least one hydroxyl group is replaced by an –O-alkyl or another organic group. They can be represented by the structure formula RCOOR’ and are usually formed by the reaction between an acid and an alcohol with elimination of water.	Ester
D004987	Ethers	Organic compounds having two alkyl or aryl groups bonded to an oxygen atom, as in the formula R1–O–R2.
D000096	Acetone	A colorless liquid used as a solvent and an antiseptic. It is one of the ketone bodies produced during ketoacidosis.
D000480	Alkynes	Hydrocarbons with at least one triple bond in the linear portion, of the general formula Cn-H2n-2.	Acetylenic Compounds,Alkyne,Acetylenes
D015394	Molecular Structure	The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds.	Structure, Molecular,Molecular Structures,Structures, Molecular