Control of chemoselectivity in dirhodium(II)-catalyzed reaction of 5,6- dioxygenated 2-diazo-3-oxohexanoates: C-H insertion reaction versus oxonium ylide formation

Takayuki Yakura; Akiharu Ueki; Yukiko Morioka; Toyoshige Kurata; Kenji Tanaka; Masazumi Ikeda

doi:10.1248/cpb.46.1182

Control of chemoselectivity in dirhodium(II)-catalyzed reaction of 5,6- dioxygenated 2-diazo-3-oxohexanoates: C-H insertion reaction versus oxonium ylide formation

Takayuki Yakura^*, Akiharu Ueki, Yukiko Morioka, Toyoshige Kurata, Kenji Tanaka, Masazumi Ikeda

^*この論文の責任著者

分子合成化学研究室

研究成果: ジャーナルへの寄稿 › 学術論文 › 査読

10 被引用数 (Scopus)

抄録

Methyl (S)-2-diazo-4-(3,3-dimethyl-2,4-dioxolan-1-yl)-3-oxobutanoate (1), upon treatment with Rh₂(OAc)₄ in boiling dichloromethane, gave methyl (1S,5S)-2,2-dimethyl-7-oxo-3,8-dioxabicyclo[3,2.1]octane-1-carboxylate (2) via oxonium ylide formation/1,2-shift. On the other hand, similar treatment of methyl (S)-5,6-bis(tertbutyldimethylsilyloxy)-2-diazo-3-oxohexanoate (3a) gave methyl 3-(tert-butyldimethylsilyloxy)-5-oxo-1-cyclopentene-1-carboxylate (4a) via the C-H insertion reaction.

本文言語	英語
ページ（範囲）	1182-1183
ページ数	2
ジャーナル	Chemical and Pharmaceutical Bulletin
巻	46
号	7
DOI	https://doi.org/10.1248/cpb.46.1182
出版ステータス	出版済み - 1998

ASJC Scopus 主題領域

化学一般
創薬

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10.1248/cpb.46.1182

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「Control of chemoselectivity in dirhodium(II)-catalyzed reaction of 5,6- dioxygenated 2-diazo-3-oxohexanoates: C-H insertion reaction versus oxonium ylide formation」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

引用スタイル

@article{31cb0c4087ce4b959e04262dc1e5e27f,

title = "Control of chemoselectivity in dirhodium(II)-catalyzed reaction of 5,6- dioxygenated 2-diazo-3-oxohexanoates: C-H insertion reaction versus oxonium ylide formation",

abstract = "Methyl (S)-2-diazo-4-(3,3-dimethyl-2,4-dioxolan-1-yl)-3-oxobutanoate (1), upon treatment with Rh2(OAc)4 in boiling dichloromethane, gave methyl (1S,5S)-2,2-dimethyl-7-oxo-3,8-dioxabicyclo[3,2.1]octane-1-carboxylate (2) via oxonium ylide formation/1,2-shift. On the other hand, similar treatment of methyl (S)-5,6-bis(tertbutyldimethylsilyloxy)-2-diazo-3-oxohexanoate (3a) gave methyl 3-(tert-butyldimethylsilyloxy)-5-oxo-1-cyclopentene-1-carboxylate (4a) via the C-H insertion reaction.",

keywords = "1,2-shift, C-H insertion reaction, Cyclopentenone, Diazoketone, Dirhodium(II) catalyst, Oxonium ylide",

author = "Takayuki Yakura and Akiharu Ueki and Yukiko Morioka and Toyoshige Kurata and Kenji Tanaka and Masazumi Ikeda",

year = "1998",

doi = "10.1248/cpb.46.1182",

language = "英語",

volume = "46",

pages = "1182--1183",

journal = "Chemical and Pharmaceutical Bulletin",

issn = "0009-2363",

publisher = "Pharmaceutical Society of Japan",

number = "7",

}

Control of chemoselectivity in dirhodium(II)-catalyzed reaction of 5,6- dioxygenated 2-diazo-3-oxohexanoates: C-H insertion reaction versus oxonium ylide formation. / Yakura, Takayuki; Ueki, Akiharu; Morioka, Yukiko その他.
In: Chemical and Pharmaceutical Bulletin, Vol. 46, No. 7, 1998, p. 1182-1183.

研究成果: ジャーナルへの寄稿 › 学術論文 › 査読

TY - JOUR

T1 - Control of chemoselectivity in dirhodium(II)-catalyzed reaction of 5,6- dioxygenated 2-diazo-3-oxohexanoates

T2 - C-H insertion reaction versus oxonium ylide formation

AU - Yakura, Takayuki

AU - Ueki, Akiharu

AU - Morioka, Yukiko

AU - Kurata, Toyoshige

AU - Tanaka, Kenji

AU - Ikeda, Masazumi

PY - 1998

Y1 - 1998

N2 - Methyl (S)-2-diazo-4-(3,3-dimethyl-2,4-dioxolan-1-yl)-3-oxobutanoate (1), upon treatment with Rh2(OAc)4 in boiling dichloromethane, gave methyl (1S,5S)-2,2-dimethyl-7-oxo-3,8-dioxabicyclo[3,2.1]octane-1-carboxylate (2) via oxonium ylide formation/1,2-shift. On the other hand, similar treatment of methyl (S)-5,6-bis(tertbutyldimethylsilyloxy)-2-diazo-3-oxohexanoate (3a) gave methyl 3-(tert-butyldimethylsilyloxy)-5-oxo-1-cyclopentene-1-carboxylate (4a) via the C-H insertion reaction.

AB - Methyl (S)-2-diazo-4-(3,3-dimethyl-2,4-dioxolan-1-yl)-3-oxobutanoate (1), upon treatment with Rh2(OAc)4 in boiling dichloromethane, gave methyl (1S,5S)-2,2-dimethyl-7-oxo-3,8-dioxabicyclo[3,2.1]octane-1-carboxylate (2) via oxonium ylide formation/1,2-shift. On the other hand, similar treatment of methyl (S)-5,6-bis(tertbutyldimethylsilyloxy)-2-diazo-3-oxohexanoate (3a) gave methyl 3-(tert-butyldimethylsilyloxy)-5-oxo-1-cyclopentene-1-carboxylate (4a) via the C-H insertion reaction.

KW - 1,2-shift

KW - C-H insertion reaction

KW - Cyclopentenone

KW - Diazoketone

KW - Dirhodium(II) catalyst

KW - Oxonium ylide

UR - http://www.scopus.com/inward/record.url?scp=0031827988&partnerID=8YFLogxK

U2 - 10.1248/cpb.46.1182

DO - 10.1248/cpb.46.1182

M3 - 学術論文

AN - SCOPUS:0031827988

SN - 0009-2363

VL - 46

SP - 1182

EP - 1183

JO - Chemical and Pharmaceutical Bulletin

JF - Chemical and Pharmaceutical Bulletin

IS - 7

ER -