Synthesis of α- and/or γ-benzoyloxy-α,β-enones from α-halo-α,β-enones

Yujiro Hayashi; Mitsuru Shoji; Satoshi Kishida

doi:10.1016/j.tetlet.2004.11.119

Synthesis of α- and/or γ-benzoyloxy-α,β-enones from α-halo-α,β-enones

Yujiro Hayashi, Mitsuru Shoji, Satoshi Kishida

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

10 Citations (Scopus)

Abstract

Sodium benzoate reacts with α-halo-α,β-enones in the presence of tetrabutylammonium hydrogensulfate or 18-Crown-6 to afford α- and/or γ-benzoyloxylated α,β-enones in good yield. The α/γ and γ/γ′ selectivities are dependent on the substrate and reagent. Sodium benzoate reacts with α-halo-α,β- enones in the presence of tetrabutylammonium hydrogensulfate or 18-Crown-6 to afford α- and/or γ-benzoyloxy-α,β-enones in good yield. The α/γ and γ/γ′ selectivities are dependent on the substrate and reagent.

Original language	English
Pages (from-to)	681-685
Number of pages	5
Journal	Tetrahedron Letters
Volume	46
Issue number	4
DOIs	https://doi.org/10.1016/j.tetlet.2004.11.119
Publication status	Published - 2005 Jan 24
Externally published	Yes

Keywords

Ammonium salt
Crown ether
Enones
Substitution

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2004.11.119

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title = "Synthesis of α- and/or γ-benzoyloxy-α,β-enones from α-halo-α,β-enones",

abstract = "Sodium benzoate reacts with α-halo-α,β-enones in the presence of tetrabutylammonium hydrogensulfate or 18-Crown-6 to afford α- and/or γ-benzoyloxylated α,β-enones in good yield. The α/γ and γ/γ′ selectivities are dependent on the substrate and reagent. Sodium benzoate reacts with α-halo-α,β- enones in the presence of tetrabutylammonium hydrogensulfate or 18-Crown-6 to afford α- and/or γ-benzoyloxy-α,β-enones in good yield. The α/γ and γ/γ′ selectivities are dependent on the substrate and reagent.",

keywords = "Ammonium salt, Crown ether, Enones, Substitution",

author = "Yujiro Hayashi and Mitsuru Shoji and Satoshi Kishida",

note = "Funding Information: This work was supported by a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology, Japan.",

year = "2005",

month = jan,

day = "24",

doi = "10.1016/j.tetlet.2004.11.119",

language = "English",

volume = "46",

pages = "681--685",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "4",

}

TY - JOUR

T1 - Synthesis of α- and/or γ-benzoyloxy-α,β-enones from α-halo-α,β-enones

AU - Hayashi, Yujiro

AU - Shoji, Mitsuru

AU - Kishida, Satoshi

N1 - Funding Information: This work was supported by a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology, Japan.

PY - 2005/1/24

Y1 - 2005/1/24

N2 - Sodium benzoate reacts with α-halo-α,β-enones in the presence of tetrabutylammonium hydrogensulfate or 18-Crown-6 to afford α- and/or γ-benzoyloxylated α,β-enones in good yield. The α/γ and γ/γ′ selectivities are dependent on the substrate and reagent. Sodium benzoate reacts with α-halo-α,β- enones in the presence of tetrabutylammonium hydrogensulfate or 18-Crown-6 to afford α- and/or γ-benzoyloxy-α,β-enones in good yield. The α/γ and γ/γ′ selectivities are dependent on the substrate and reagent.

AB - Sodium benzoate reacts with α-halo-α,β-enones in the presence of tetrabutylammonium hydrogensulfate or 18-Crown-6 to afford α- and/or γ-benzoyloxylated α,β-enones in good yield. The α/γ and γ/γ′ selectivities are dependent on the substrate and reagent. Sodium benzoate reacts with α-halo-α,β- enones in the presence of tetrabutylammonium hydrogensulfate or 18-Crown-6 to afford α- and/or γ-benzoyloxy-α,β-enones in good yield. The α/γ and γ/γ′ selectivities are dependent on the substrate and reagent.

KW - Ammonium salt

KW - Crown ether

KW - Enones

KW - Substitution

UR - http://www.scopus.com/inward/record.url?scp=11144250824&partnerID=8YFLogxK

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U2 - 10.1016/j.tetlet.2004.11.119

DO - 10.1016/j.tetlet.2004.11.119

M3 - Article

AN - SCOPUS:11144250824

SN - 0040-4039

VL - 46

SP - 681

EP - 685

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 4

ER -

Synthesis of α- and/or γ-benzoyloxy-α,β-enones from α-halo-α,β-enones

Abstract

Keywords

ASJC Scopus subject areas

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