Chiral Aryl Iodide-Catalyzed Enantioselective α-Oxidation of Ketones

Arantxa Rodríguez; Wesley J. Moran

doi:10.1055/s-0031-1290590

Chiral Aryl Iodide-Catalyzed Enantioselective α-Oxidation of Ketones

Arantxa Rodríguez, Wesley J. Moran

School of Applied Sciences

Research output: Contribution to journal › Article › peer-review

60 Citations (Scopus)

Abstract

Several chiral aryl iodides were synthesized and assessed as catalysts in the enantioselective α-oxytosylation of propiophenone and the oxidative cyclization of 5-oxo-5-phenylpentanoic acid to 5-benzoyldihydrofuran-2(3H)-one. The highest enantioselectivities obtained were 18 and 51% ee, respectively. The latter is the highest selectivity recorded to date for this reaction.

Original language	English
Pages (from-to)	1178-1182
Number of pages	5
Journal	Synthesis
Volume	44
Issue number	8
DOIs	https://doi.org/10.1055/s-0031-1290590
Publication status	Published - Apr 2012

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abstract = "Several chiral aryl iodides were synthesized and assessed as catalysts in the enantioselective α-oxytosylation of propiophenone and the oxidative cyclization of 5-oxo-5-phenylpentanoic acid to 5-benzoyldihydrofuran-2(3H)-one. The highest enantioselectivities obtained were 18 and 51% ee, respectively. The latter is the highest selectivity recorded to date for this reaction.",

keywords = "Asymmetric catalysis, Enantioselectivity, Hypervalent iodine, Organocatalysis, Oxidation",

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N2 - Several chiral aryl iodides were synthesized and assessed as catalysts in the enantioselective α-oxytosylation of propiophenone and the oxidative cyclization of 5-oxo-5-phenylpentanoic acid to 5-benzoyldihydrofuran-2(3H)-one. The highest enantioselectivities obtained were 18 and 51% ee, respectively. The latter is the highest selectivity recorded to date for this reaction.

AB - Several chiral aryl iodides were synthesized and assessed as catalysts in the enantioselective α-oxytosylation of propiophenone and the oxidative cyclization of 5-oxo-5-phenylpentanoic acid to 5-benzoyldihydrofuran-2(3H)-one. The highest enantioselectivities obtained were 18 and 51% ee, respectively. The latter is the highest selectivity recorded to date for this reaction.

KW - Asymmetric catalysis

KW - Enantioselectivity

KW - Hypervalent iodine

KW - Organocatalysis

KW - Oxidation

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U2 - 10.1055/s-0031-1290590

DO - 10.1055/s-0031-1290590

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JO - Synthesis

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ER -

Chiral Aryl Iodide-Catalyzed Enantioselective α-Oxidation of Ketones

Abstract

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