PIDA-Mediated Formal Olefinic C=C Bond Cleavage of α-Oxo-Ketene N ,N -Acetals toward Substituted Oxazolines

Autor:	Zhengkun Yu, Fei Huang, Tenglong Guo, Quanbin Jiang
Rok vydání:	2018
Předmět:	010405 organic chemistry Organic Chemistry Hypervalent molecule Ketene General Chemistry Oxazoline 010402 general chemistry 01 natural sciences Medicinal chemistry Catalysis 0104 chemical sciences chemistry.chemical_compound Hydrolysis PIDA chemistry Reagent Bond cleavage
Zdroj:	Chemistry - A European Journal. 24:14368-14372
ISSN:	0947-6539
DOI:	10.1002/chem.201803466
Popis:	The hypervalent iodine reagent PhI(OAc)2 (PIDA) mediated the formal oxidative C=C bond cleavage and subsequent cyclization of internal olefins, that is, α-oxo-ketene N,N-acetals, which afforded substituted oxazolines. Isothiazoline derivatives were obtained from the reactions of α-thioxo-ketene N,N-acetals with PIDA under the same conditions. Hydrolysis of the resultant oxazoline derivatives led to highly functionalized oxazolones. A plausible mechanism was proposed based upon the formation of isothiazoline-type intermediates.
Databáze:	OpenAIRE
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