Facile isomerization of silyl enol ethers catalyzed by triflic imide and its application to one-pot isomerization–(2 + 2) cycloaddition

A triflic imide (Tf2NH) catalyzed isomerization of kinetically favourable silyl enol ethers into thermodynamically stable ones was developed. We also demonstrated a one-pot catalytic reaction consisting of (2 + 2) cycloaddition and isomerization. In the reaction sequence, Tf2NH catalyzes both of the...

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Main Authors:	Kazato Inanaga, Yu Ogawa, Yuuki Nagamoto, Akihiro Daigaku, Hidetoshi Tokuyama, Yoshiji Takemoto, Kiyosei Takasu
Format:	Article
Language:	English
Published:	Beilstein-Institut 2012-04-01
Series:	Beilstein Journal of Organic Chemistry
Subjects:	isomerization one-pot reaction organocatalysis silyl enol ethers triflic imide
Online Access:	https://doi.org/10.3762/bjoc.8.73

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spelling	doaj-fcfa3ae1902b4128849e30ae0afed7c02021-04-02T06:59:43ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972012-04-018165866110.3762/bjoc.8.731860-5397-8-73Facile isomerization of silyl enol ethers catalyzed by triflic imide and its application to one-pot isomerization–(2 + 2) cycloadditionKazato Inanaga0Yu Ogawa1Yuuki Nagamoto2Akihiro Daigaku3Hidetoshi Tokuyama4Yoshiji Takemoto5Kiyosei Takasu6Graduate School of Pharmaceutical Sciences, Tohoku University, Aobayama, Sendai 980-8578, JapanGraduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo, Kyoto 606-8501, JapanGraduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo, Kyoto 606-8501, JapanGraduate School of Pharmaceutical Sciences, Tohoku University, Aobayama, Sendai 980-8578, JapanGraduate School of Pharmaceutical Sciences, Tohoku University, Aobayama, Sendai 980-8578, JapanGraduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo, Kyoto 606-8501, JapanGraduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo, Kyoto 606-8501, JapanA triflic imide (Tf2NH) catalyzed isomerization of kinetically favourable silyl enol ethers into thermodynamically stable ones was developed. We also demonstrated a one-pot catalytic reaction consisting of (2 + 2) cycloaddition and isomerization. In the reaction sequence, Tf2NH catalyzes both of the reactions.https://doi.org/10.3762/bjoc.8.73isomerizationone-pot reactionorganocatalysissilyl enol etherstriflic imide
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Kazato Inanaga Yu Ogawa Yuuki Nagamoto Akihiro Daigaku Hidetoshi Tokuyama Yoshiji Takemoto Kiyosei Takasu
spellingShingle	Kazato Inanaga Yu Ogawa Yuuki Nagamoto Akihiro Daigaku Hidetoshi Tokuyama Yoshiji Takemoto Kiyosei Takasu Facile isomerization of silyl enol ethers catalyzed by triflic imide and its application to one-pot isomerization–(2 + 2) cycloaddition Beilstein Journal of Organic Chemistry isomerization one-pot reaction organocatalysis silyl enol ethers triflic imide
author_facet	Kazato Inanaga Yu Ogawa Yuuki Nagamoto Akihiro Daigaku Hidetoshi Tokuyama Yoshiji Takemoto Kiyosei Takasu
author_sort	Kazato Inanaga
title	Facile isomerization of silyl enol ethers catalyzed by triflic imide and its application to one-pot isomerization–(2 + 2) cycloaddition
title_short	Facile isomerization of silyl enol ethers catalyzed by triflic imide and its application to one-pot isomerization–(2 + 2) cycloaddition
title_full	Facile isomerization of silyl enol ethers catalyzed by triflic imide and its application to one-pot isomerization–(2 + 2) cycloaddition
title_fullStr	Facile isomerization of silyl enol ethers catalyzed by triflic imide and its application to one-pot isomerization–(2 + 2) cycloaddition
title_full_unstemmed	Facile isomerization of silyl enol ethers catalyzed by triflic imide and its application to one-pot isomerization–(2 + 2) cycloaddition
title_sort	facile isomerization of silyl enol ethers catalyzed by triflic imide and its application to one-pot isomerization–(2 + 2) cycloaddition
publisher	Beilstein-Institut
series	Beilstein Journal of Organic Chemistry
issn	1860-5397
publishDate	2012-04-01
description	A triflic imide (Tf2NH) catalyzed isomerization of kinetically favourable silyl enol ethers into thermodynamically stable ones was developed. We also demonstrated a one-pot catalytic reaction consisting of (2 + 2) cycloaddition and isomerization. In the reaction sequence, Tf2NH catalyzes both of the reactions.
topic	isomerization one-pot reaction organocatalysis silyl enol ethers triflic imide
url	https://doi.org/10.3762/bjoc.8.73
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Facile isomerization of silyl enol ethers catalyzed by triflic imide and its application to one-pot isomerization–(2 + 2) cycloaddition

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