Direct β‑Acyloxylation of Enamines via PhIO-Mediated Intermolecular Oxidative C–O Bond Formation and Its Application to the Synthesis of Oxazoles

Direct β‑Acyloxylation of Enamines via PhIO-Mediated Intermolecular Oxidative C–O Bond Formation and Its Application to the Synthesis of Oxazoles

A direct β-acyloxylation of enamine compounds has been achieved by using iodosobenzene (PhIO) as an oxidant to realize the intermolecular oxidative C(sp 2)-O bond formation between enamines and various carboxylic acids, including N-protected amino acids. The transformation tolerates a wide range of...

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Veröffentlicht in:Organic letters 2012-11, Vol.14 (21), p.5480-5483
Hauptverfasser: Liu, Xin, Cheng, Ran, Zhao, Feifei, Zhang-Negrerie, Daisy, Du, Yunfei, Zhao, Kang
Format: Artikel
Sprache:eng
Schlagworte:
Amines - chemistry
Carboxylic Acids - chemistry
Catalysis
Cyclization
Molecular Structure
Oxazoles - chemical synthesis
Oxazoles - chemistry
Oxidation-Reduction
Stereoisomerism
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Zusammenfassung:A direct β-acyloxylation of enamine compounds has been achieved by using iodosobenzene (PhIO) as an oxidant to realize the intermolecular oxidative C(sp 2)-O bond formation between enamines and various carboxylic acids, including N-protected amino acids. The transformation tolerates a wide range of functional groups and furnishes a variety of β-acyloxy enamines that can be conveniently converted to oxazole compounds via cyclodehydration.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol3025583