Practical Oppenauer (OPP) oxidation of alcohols with a modified aluminum catalyst

Takashi Ooi; Hidehito Otsuka; Tomoya Miura; Hayato Ichikawa; Keiji Maruoka

doi:10.1021/ol020094c

Practical Oppenauer (OPP) oxidation of alcohols with a modified aluminum catalyst

Takashi Ooi, Hidehito Otsuka, Tomoya Miura, Hayato Ichikawa, Keiji Maruoka

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

52 Citations (Scopus)

Abstract

(Matrix presented) Modified aluminum catalyst 2 was found to be highly effective for Oppenauer (OPP) oxidation of alcohols under mild conditions. For example, oxidation of carveol in toluene with t-BuCHO (1.2 equiv) as a hydride acceptor in the presence of 2 (1 mol %) proceeded smoothly at 21°C to give carvone in 94% yield after 1 h. A practical aspect of this system was highlighted by the facile OPP oxidation of terpenoids and steroids with 1.2-3.0 equiv of acetone and 2 (3-5 mol %).

Original language	English
Pages (from-to)	2669-2672
Number of pages	4
Journal	Organic Letters
Volume	4
Issue number	16
DOIs	https://doi.org/10.1021/ol020094c
Publication status	Published - Aug 8 2002
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "(Matrix presented) Modified aluminum catalyst 2 was found to be highly effective for Oppenauer (OPP) oxidation of alcohols under mild conditions. For example, oxidation of carveol in toluene with t-BuCHO (1.2 equiv) as a hydride acceptor in the presence of 2 (1 mol %) proceeded smoothly at 21°C to give carvone in 94% yield after 1 h. A practical aspect of this system was highlighted by the facile OPP oxidation of terpenoids and steroids with 1.2-3.0 equiv of acetone and 2 (3-5 mol %).",

author = "Takashi Ooi and Hidehito Otsuka and Tomoya Miura and Hayato Ichikawa and Keiji Maruoka",

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AU - Ooi, Takashi

AU - Otsuka, Hidehito

AU - Miura, Tomoya

AU - Ichikawa, Hayato

AU - Maruoka, Keiji

PY - 2002/8/8

Y1 - 2002/8/8

N2 - (Matrix presented) Modified aluminum catalyst 2 was found to be highly effective for Oppenauer (OPP) oxidation of alcohols under mild conditions. For example, oxidation of carveol in toluene with t-BuCHO (1.2 equiv) as a hydride acceptor in the presence of 2 (1 mol %) proceeded smoothly at 21°C to give carvone in 94% yield after 1 h. A practical aspect of this system was highlighted by the facile OPP oxidation of terpenoids and steroids with 1.2-3.0 equiv of acetone and 2 (3-5 mol %).

AB - (Matrix presented) Modified aluminum catalyst 2 was found to be highly effective for Oppenauer (OPP) oxidation of alcohols under mild conditions. For example, oxidation of carveol in toluene with t-BuCHO (1.2 equiv) as a hydride acceptor in the presence of 2 (1 mol %) proceeded smoothly at 21°C to give carvone in 94% yield after 1 h. A practical aspect of this system was highlighted by the facile OPP oxidation of terpenoids and steroids with 1.2-3.0 equiv of acetone and 2 (3-5 mol %).

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Practical Oppenauer (OPP) oxidation of alcohols with a modified aluminum catalyst

Abstract

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