Metal complexes-catalyzed hydrolysis and alcoholysis of organic substrates and their application to kinetic resolution

Makoto Tokunaga; Hiroshi Aoyama; Junya Kiyosu; Yuki Shirogane; Tetsuo Iwasawa; Yasushi Obora; Yasushi Tsuji

doi:10.1016/j.jorganchem.2006.06.045

Metal complexes-catalyzed hydrolysis and alcoholysis of organic substrates and their application to kinetic resolution

Makoto Tokunaga, Hiroshi Aoyama, Junya Kiyosu, Yuki Shirogane, Tetsuo Iwasawa, Yasushi Obora, Yasushi Tsuji

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

19 Citations (Scopus)

Abstract

Metal complexes-catalyzed hydrolysis and alcoholysis of organic substrates such as alkenyl esters, alkenyl ethers, and azlactones (oxazol-5(4H)-ones) are described. These reactions were applied for kinetic resolution of chiral compounds and high selectivities were achieved with vinyl ethers of 2-substituted cyclohexanols, 1,1′-bi-2-naphthols, 1,1′-bi-2-phenols, and 4,4-disubstituted azlactones. Oxidative carbon-carbon bond cleavage reactions, which were found in the course of the study of asymmetric hydrolysis were also described.

Original language	English
Pages (from-to)	472-480
Number of pages	9
Journal	Journal of Organometallic Chemistry
Volume	692
Issue number	1-3
DOIs	https://doi.org/10.1016/j.jorganchem.2006.06.045
Publication status	Published - Jan 1 2007
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry
Materials Chemistry

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10.1016/j.jorganchem.2006.06.045

Cite this

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title = "Metal complexes-catalyzed hydrolysis and alcoholysis of organic substrates and their application to kinetic resolution",

abstract = "Metal complexes-catalyzed hydrolysis and alcoholysis of organic substrates such as alkenyl esters, alkenyl ethers, and azlactones (oxazol-5(4H)-ones) are described. These reactions were applied for kinetic resolution of chiral compounds and high selectivities were achieved with vinyl ethers of 2-substituted cyclohexanols, 1,1′-bi-2-naphthols, 1,1′-bi-2-phenols, and 4,4-disubstituted azlactones. Oxidative carbon-carbon bond cleavage reactions, which were found in the course of the study of asymmetric hydrolysis were also described.",

author = "Makoto Tokunaga and Hiroshi Aoyama and Junya Kiyosu and Yuki Shirogane and Tetsuo Iwasawa and Yasushi Obora and Yasushi Tsuji",

note = "Funding Information: This work was supported by Grant-in-Aid for Scientific Research on Priority Areas (No. 16033204, Reaction Control of Dynamic Complexes) from Ministry of Education, Culture, Sports, Science and Technology, Japan. We thank Takasago International Corporation for providing DTBM-SEGPHOS.",

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doi = "10.1016/j.jorganchem.2006.06.045",

language = "English",

volume = "692",

pages = "472--480",

journal = "Journal of Organometallic Chemistry",

issn = "0022-328X",

publisher = "Elsevier",

number = "1-3",

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TY - JOUR

T1 - Metal complexes-catalyzed hydrolysis and alcoholysis of organic substrates and their application to kinetic resolution

AU - Tokunaga, Makoto

AU - Aoyama, Hiroshi

AU - Kiyosu, Junya

AU - Shirogane, Yuki

AU - Iwasawa, Tetsuo

AU - Obora, Yasushi

AU - Tsuji, Yasushi

N1 - Funding Information: This work was supported by Grant-in-Aid for Scientific Research on Priority Areas (No. 16033204, Reaction Control of Dynamic Complexes) from Ministry of Education, Culture, Sports, Science and Technology, Japan. We thank Takasago International Corporation for providing DTBM-SEGPHOS.

PY - 2007/1/1

Y1 - 2007/1/1

N2 - Metal complexes-catalyzed hydrolysis and alcoholysis of organic substrates such as alkenyl esters, alkenyl ethers, and azlactones (oxazol-5(4H)-ones) are described. These reactions were applied for kinetic resolution of chiral compounds and high selectivities were achieved with vinyl ethers of 2-substituted cyclohexanols, 1,1′-bi-2-naphthols, 1,1′-bi-2-phenols, and 4,4-disubstituted azlactones. Oxidative carbon-carbon bond cleavage reactions, which were found in the course of the study of asymmetric hydrolysis were also described.

AB - Metal complexes-catalyzed hydrolysis and alcoholysis of organic substrates such as alkenyl esters, alkenyl ethers, and azlactones (oxazol-5(4H)-ones) are described. These reactions were applied for kinetic resolution of chiral compounds and high selectivities were achieved with vinyl ethers of 2-substituted cyclohexanols, 1,1′-bi-2-naphthols, 1,1′-bi-2-phenols, and 4,4-disubstituted azlactones. Oxidative carbon-carbon bond cleavage reactions, which were found in the course of the study of asymmetric hydrolysis were also described.

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DO - 10.1016/j.jorganchem.2006.06.045

M3 - Article

AN - SCOPUS:33845766187

SN - 0022-328X

VL - 692

SP - 472

EP - 480

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

IS - 1-3

ER -

Metal complexes-catalyzed hydrolysis and alcoholysis of organic substrates and their application to kinetic resolution

Abstract

All Science Journal Classification (ASJC) codes

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