Co-catalyzed autoxidation of alkene in the presence of silane. The effect of the structure of silanes on the efficiency of the reaction and on the product distribution

Jin Ming Wu; Shigeki Kunikawa; Takahiro Tokuyasu; Araki Masuyama; Masatomo Nojima; Hye Sook Kim; Yusuke Wataya

doi:10.1016/j.tet.2005.08.025

Co-catalyzed autoxidation of alkene in the presence of silane. The effect of the structure of silanes on the efficiency of the reaction and on the product distribution

Jin Ming Wu, Shigeki Kunikawa, Takahiro Tokuyasu, Araki Masuyama, Masatomo Nojima, Hye Sook Kim, Yusuke Wataya

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

16 Citations (Scopus)

Abstract

A systematic investigation of the structural effect of silanes on the Co-catalyzed reductive oxygenation of alkene in the presence of silane (Mukaiyama-Isayama reaction) showed that the efficiency of the reaction decreases with the increase of the steric bulk of the silanes. A similar trend was observed for the metal-exchange reaction between Co(III)-alkylperoxo complex and silane, too. The peroxidation of (S)-limonene, followed by deprotection of the derived silyl peroxides, provides a mixture of the corresponding monocyclic hydroperoxide 24 and the bicyclic one 25, the ratio being a marked function of the steric bulk of silanes.

Original language	English
Pages (from-to)	9961-9968
Number of pages	8
Journal	Tetrahedron
Volume	61
Issue number	42
DOIs	https://doi.org/10.1016/j.tet.2005.08.025
Publication status	Published - Oct 17 2005

Keywords

Antimalarial activity
Co-catalyzed autoxidation
Silyl peroxide
Yingzhaosu A analogue

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2005.08.025

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title = "Co-catalyzed autoxidation of alkene in the presence of silane. The effect of the structure of silanes on the efficiency of the reaction and on the product distribution",

abstract = "A systematic investigation of the structural effect of silanes on the Co-catalyzed reductive oxygenation of alkene in the presence of silane (Mukaiyama-Isayama reaction) showed that the efficiency of the reaction decreases with the increase of the steric bulk of the silanes. A similar trend was observed for the metal-exchange reaction between Co(III)-alkylperoxo complex and silane, too. The peroxidation of (S)-limonene, followed by deprotection of the derived silyl peroxides, provides a mixture of the corresponding monocyclic hydroperoxide 24 and the bicyclic one 25, the ratio being a marked function of the steric bulk of silanes.",

keywords = "Antimalarial activity, Co-catalyzed autoxidation, Silyl peroxide, Yingzhaosu A analogue",

author = "Wu, {Jin Ming} and Shigeki Kunikawa and Takahiro Tokuyasu and Araki Masuyama and Masatomo Nojima and Kim, {Hye Sook} and Yusuke Wataya",

note = "Funding Information: This work was supported by the Grant-in-Aid for Scientific Research on Priority Areas from the Ministry of Education, Science, Sports and Culture of Japan (15019060 and 14021072) and by the Program for Promotion of Fundamental Studies in Health Sciences of the Pharmaceuticals and Medical Devices Agency (PMDA).",

year = "2005",

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doi = "10.1016/j.tet.2005.08.025",

language = "English",

volume = "61",

pages = "9961--9968",

journal = "Tetrahedron",

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AU - Wu, Jin Ming

AU - Kunikawa, Shigeki

AU - Tokuyasu, Takahiro

AU - Masuyama, Araki

AU - Nojima, Masatomo

AU - Kim, Hye Sook

AU - Wataya, Yusuke

N1 - Funding Information: This work was supported by the Grant-in-Aid for Scientific Research on Priority Areas from the Ministry of Education, Science, Sports and Culture of Japan (15019060 and 14021072) and by the Program for Promotion of Fundamental Studies in Health Sciences of the Pharmaceuticals and Medical Devices Agency (PMDA).

PY - 2005/10/17

Y1 - 2005/10/17

N2 - A systematic investigation of the structural effect of silanes on the Co-catalyzed reductive oxygenation of alkene in the presence of silane (Mukaiyama-Isayama reaction) showed that the efficiency of the reaction decreases with the increase of the steric bulk of the silanes. A similar trend was observed for the metal-exchange reaction between Co(III)-alkylperoxo complex and silane, too. The peroxidation of (S)-limonene, followed by deprotection of the derived silyl peroxides, provides a mixture of the corresponding monocyclic hydroperoxide 24 and the bicyclic one 25, the ratio being a marked function of the steric bulk of silanes.

AB - A systematic investigation of the structural effect of silanes on the Co-catalyzed reductive oxygenation of alkene in the presence of silane (Mukaiyama-Isayama reaction) showed that the efficiency of the reaction decreases with the increase of the steric bulk of the silanes. A similar trend was observed for the metal-exchange reaction between Co(III)-alkylperoxo complex and silane, too. The peroxidation of (S)-limonene, followed by deprotection of the derived silyl peroxides, provides a mixture of the corresponding monocyclic hydroperoxide 24 and the bicyclic one 25, the ratio being a marked function of the steric bulk of silanes.

KW - Antimalarial activity

KW - Co-catalyzed autoxidation

KW - Silyl peroxide

KW - Yingzhaosu A analogue

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JO - Tetrahedron

JF - Tetrahedron

IS - 42

ER -

Co-catalyzed autoxidation of alkene in the presence of silane. The effect of the structure of silanes on the efficiency of the reaction and on the product distribution

Abstract

Keywords

ASJC Scopus subject areas

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