Cobalt-catalyzed oxidative kinetic resolution of secondary benzylic alcohols with molecular oxygen

Tohru Yamada; Sho Higano; Takanori Yano; Yoshihiro Yamashita

doi:10.1246/cl.2009.40

Cobalt-catalyzed oxidative kinetic resolution of secondary benzylic alcohols with molecular oxygen

Tohru Yamada, Sho Higano, Takanori Yano, Yoshihiro Yamashita

Department of Chemistry

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

19 Citations (Scopus)

Abstract

The oxidative kinetic resolution of secondary alcohols using molecular oxygen and olefins was catalyzed by the optically active ketoiminatocobalt(II) complexes. The various secondary benzylic alcohols were subjected to the aerobic oxidative reaction to afford optically active alcohols of high ee along with the corresponding ketones in high yield. The oxidation of the deuterated alcohols revealed that the accompanying olefin mediated the oxidation for conversion to the corresponding α-deuterated ketones.

Original language	English
Pages (from-to)	40-41
Number of pages	2
Journal	Chemistry Letters
Volume	38
Issue number	1
DOIs	https://doi.org/10.1246/cl.2009.40
Publication status	Published - 2009

ASJC Scopus subject areas

Chemistry(all)

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10.1246/cl.2009.40

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abstract = "The oxidative kinetic resolution of secondary alcohols using molecular oxygen and olefins was catalyzed by the optically active ketoiminatocobalt(II) complexes. The various secondary benzylic alcohols were subjected to the aerobic oxidative reaction to afford optically active alcohols of high ee along with the corresponding ketones in high yield. The oxidation of the deuterated alcohols revealed that the accompanying olefin mediated the oxidation for conversion to the corresponding α-deuterated ketones.",

author = "Tohru Yamada and Sho Higano and Takanori Yano and Yoshihiro Yamashita",

note = "Funding Information: We gratefully acknowledge the U.S. National Science Foundation, through grants IIS-0120663 and DMI-0522382, and the support of the Georgia Tech Rapid Prototyping and Manufacturing Institute member companies, particularly Pratt & Whitney, for sponsoring this work.",

year = "2009",

doi = "10.1246/cl.2009.40",

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T1 - Cobalt-catalyzed oxidative kinetic resolution of secondary benzylic alcohols with molecular oxygen

AU - Yamada, Tohru

AU - Higano, Sho

AU - Yano, Takanori

AU - Yamashita, Yoshihiro

N1 - Funding Information: We gratefully acknowledge the U.S. National Science Foundation, through grants IIS-0120663 and DMI-0522382, and the support of the Georgia Tech Rapid Prototyping and Manufacturing Institute member companies, particularly Pratt & Whitney, for sponsoring this work.

PY - 2009

Y1 - 2009

N2 - The oxidative kinetic resolution of secondary alcohols using molecular oxygen and olefins was catalyzed by the optically active ketoiminatocobalt(II) complexes. The various secondary benzylic alcohols were subjected to the aerobic oxidative reaction to afford optically active alcohols of high ee along with the corresponding ketones in high yield. The oxidation of the deuterated alcohols revealed that the accompanying olefin mediated the oxidation for conversion to the corresponding α-deuterated ketones.

AB - The oxidative kinetic resolution of secondary alcohols using molecular oxygen and olefins was catalyzed by the optically active ketoiminatocobalt(II) complexes. The various secondary benzylic alcohols were subjected to the aerobic oxidative reaction to afford optically active alcohols of high ee along with the corresponding ketones in high yield. The oxidation of the deuterated alcohols revealed that the accompanying olefin mediated the oxidation for conversion to the corresponding α-deuterated ketones.

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Cobalt-catalyzed oxidative kinetic resolution of secondary benzylic alcohols with molecular oxygen

Abstract

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