Practical and environmentally friendly transformation of tetrahydrofuran- 2-methanols to γ-lactones via oxidative cleavage

Tomoya Fujiwara; Yuto Horiuchi; Akihiro Yamada; Hisanori Nambu; Takayuki Yakura

doi:10.1007/978-981-10-3421-3_13

Practical and environmentally friendly transformation of tetrahydrofuran- 2-methanols to γ-lactones via oxidative cleavage

Tomoya Fujiwara, Yuto Horiuchi, Akihiro Yamada, Hisanori Nambu, Takayuki Yakura^*

^*Corresponding author for this work

Synthetic and Biomolecular Organic Chemistry

Research output: Chapter in Book/Report/Conference proceeding › Chapter › peer-review

2 Scopus citations

Abstract

Transformation of oxacycle-2-methanols to the corresponding lactones is often applied to total synthesis of natural products. It is accomplished by either direct oxidative cleavage reaction using a heavy metal oxidant or multistep conversion. As a practical and environmentally friendly procedure, a direct oxidative cleavage reaction of tetrahydrofuran-2-methanols to the corresponding c-lactones was developed. This new catalytic reaction proceeds with a catalytic amount of 2-iodobenzamide and stoichiometric Oxone (2KHSO₅.KHSO₄.K2SO₄) at room temperature.

Original language	English
Title of host publication	New Horizons of Process Chemistry
Subtitle of host publication	Scalable Reactions and Technologies
Publisher	Springer Singapore
Pages	179-190
Number of pages	12
ISBN (Electronic)	9789811034213
ISBN (Print)	9789811034206
DOIs	https://doi.org/10.1007/978-981-10-3421-3_13
State	Published - 2017/01/01

Keywords

Catalysis
Green chemistry
Hypervalent iodine
Oxidative cleavage
Oxone

ASJC Scopus subject areas

General Chemistry
General Chemical Engineering
General Medicine
General Engineering
General Agricultural and Biological Sciences

Access to Document

10.1007/978-981-10-3421-3_13

Cite this

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abstract = "Transformation of oxacycle-2-methanols to the corresponding lactones is often applied to total synthesis of natural products. It is accomplished by either direct oxidative cleavage reaction using a heavy metal oxidant or multistep conversion. As a practical and environmentally friendly procedure, a direct oxidative cleavage reaction of tetrahydrofuran-2-methanols to the corresponding c-lactones was developed. This new catalytic reaction proceeds with a catalytic amount of 2-iodobenzamide and stoichiometric Oxone (2KHSO5.KHSO4.K2SO4) at room temperature.",

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Practical and environmentally friendly transformation of tetrahydrofuran- 2-methanols to γ-lactones via oxidative cleavage. / Fujiwara, Tomoya; Horiuchi, Yuto; Yamada, Akihiro et al.
New Horizons of Process Chemistry: Scalable Reactions and Technologies. Springer Singapore, 2017. p. 179-190.

Research output: Chapter in Book/Report/Conference proceeding › Chapter › peer-review

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T1 - Practical and environmentally friendly transformation of tetrahydrofuran- 2-methanols to γ-lactones via oxidative cleavage

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AU - Horiuchi, Yuto

AU - Yamada, Akihiro

AU - Nambu, Hisanori

AU - Yakura, Takayuki

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Y1 - 2017/1/1

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AB - Transformation of oxacycle-2-methanols to the corresponding lactones is often applied to total synthesis of natural products. It is accomplished by either direct oxidative cleavage reaction using a heavy metal oxidant or multistep conversion. As a practical and environmentally friendly procedure, a direct oxidative cleavage reaction of tetrahydrofuran-2-methanols to the corresponding c-lactones was developed. This new catalytic reaction proceeds with a catalytic amount of 2-iodobenzamide and stoichiometric Oxone (2KHSO5.KHSO4.K2SO4) at room temperature.

KW - Catalysis

KW - Green chemistry

KW - Hypervalent iodine

KW - Oxidative cleavage

KW - Oxone

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BT - New Horizons of Process Chemistry

PB - Springer Singapore

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Practical and environmentally friendly transformation of tetrahydrofuran- 2-methanols to γ-lactones via oxidative cleavage

Abstract

Keywords

ASJC Scopus subject areas

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