Reaction modes of oxidative dimerization of epoxycyclohexenols

Mitsuru Shoji; Satoshi Kishida; Yusuke Kodera; Isamu Shiina; Hideaki Kakeya; Hiroyuki Osada; Yujiro Hayashi

doi:10.1016/S0040-4039(03)01781-7

Reaction modes of oxidative dimerization of epoxycyclohexenols

Mitsuru Shoji, Satoshi Kishida, Yusuke Kodera, Isamu Shiina, Hideaki Kakeya, Hiroyuki Osada, Yujiro Hayashi

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

28 Citations (Scopus)

Abstract

Of the 16 possible modes of the oxidation-6π-electrocylization-Diels-Alder reaction cascade for an epoxyquinone, and eight for a 2-alkenyl-3-hydroxymethyl-2-cyclohexen-1-one, only the endo-anti(epoxide)-anti(Me)-hetero and endo-anti(Me)-hetero are respectively observed, while both the endo-anti(epoxide)-anti(Me)-hetero and exo-anti(epoxide)-anti(Me)-homo reaction modes occur with epoxy-4-hydroxycyclohexenones owing to a hydrogen-bonding interaction.

Original language	English
Pages (from-to)	7205-7207
Number of pages	3
Journal	Tetrahedron Letters
Volume	44
Issue number	38
DOIs	https://doi.org/10.1016/S0040-4039(03)01781-7
Publication status	Published - 2003 Sept 15
Externally published	Yes

Keywords

6π-electrocylization
Diels-Alder reaction
Epoxyquinol
Hydrogen-bonding

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(03)01781-7

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title = "Reaction modes of oxidative dimerization of epoxycyclohexenols",

abstract = "Of the 16 possible modes of the oxidation-6π-electrocylization-Diels-Alder reaction cascade for an epoxyquinone, and eight for a 2-alkenyl-3-hydroxymethyl-2-cyclohexen-1-one, only the endo-anti(epoxide)-anti(Me)-hetero and endo-anti(Me)-hetero are respectively observed, while both the endo-anti(epoxide)-anti(Me)-hetero and exo-anti(epoxide)-anti(Me)-homo reaction modes occur with epoxy-4-hydroxycyclohexenones owing to a hydrogen-bonding interaction.",

keywords = "6π-electrocylization, Diels-Alder reaction, Epoxyquinol, Hydrogen-bonding",

author = "Mitsuru Shoji and Satoshi Kishida and Yusuke Kodera and Isamu Shiina and Hideaki Kakeya and Hiroyuki Osada and Yujiro Hayashi",

note = "Funding Information: This work was supported by a Grant-in-Aid for Scientific Research on Priority Areas (A) {\textquoteleft}Exploitation of Multi-Element Cyclic Molecules{\textquoteright} from the Ministry of Education, Culture, Sports, Science and Technology, Japan.",

year = "2003",

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day = "15",

doi = "10.1016/S0040-4039(03)01781-7",

language = "English",

volume = "44",

pages = "7205--7207",

journal = "Tetrahedron Letters",

issn = "0040-4039",

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TY - JOUR

T1 - Reaction modes of oxidative dimerization of epoxycyclohexenols

AU - Shoji, Mitsuru

AU - Kishida, Satoshi

AU - Kodera, Yusuke

AU - Shiina, Isamu

AU - Kakeya, Hideaki

AU - Osada, Hiroyuki

AU - Hayashi, Yujiro

N1 - Funding Information: This work was supported by a Grant-in-Aid for Scientific Research on Priority Areas (A) ‘Exploitation of Multi-Element Cyclic Molecules’ from the Ministry of Education, Culture, Sports, Science and Technology, Japan.

PY - 2003/9/15

Y1 - 2003/9/15

N2 - Of the 16 possible modes of the oxidation-6π-electrocylization-Diels-Alder reaction cascade for an epoxyquinone, and eight for a 2-alkenyl-3-hydroxymethyl-2-cyclohexen-1-one, only the endo-anti(epoxide)-anti(Me)-hetero and endo-anti(Me)-hetero are respectively observed, while both the endo-anti(epoxide)-anti(Me)-hetero and exo-anti(epoxide)-anti(Me)-homo reaction modes occur with epoxy-4-hydroxycyclohexenones owing to a hydrogen-bonding interaction.

AB - Of the 16 possible modes of the oxidation-6π-electrocylization-Diels-Alder reaction cascade for an epoxyquinone, and eight for a 2-alkenyl-3-hydroxymethyl-2-cyclohexen-1-one, only the endo-anti(epoxide)-anti(Me)-hetero and endo-anti(Me)-hetero are respectively observed, while both the endo-anti(epoxide)-anti(Me)-hetero and exo-anti(epoxide)-anti(Me)-homo reaction modes occur with epoxy-4-hydroxycyclohexenones owing to a hydrogen-bonding interaction.

KW - 6π-electrocylization

KW - Diels-Alder reaction

KW - Epoxyquinol

KW - Hydrogen-bonding

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U2 - 10.1016/S0040-4039(03)01781-7

DO - 10.1016/S0040-4039(03)01781-7

M3 - Article

AN - SCOPUS:0043011180

SN - 0040-4039

VL - 44

SP - 7205

EP - 7207

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 38

ER -

Reaction modes of oxidative dimerization of epoxycyclohexenols

Abstract

Keywords

ASJC Scopus subject areas

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