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

Kazato Inanaga; Yu Ogawa; Yuuki Nagamoto; Akihiro Daigaku; Hidetoshi Tokuyama; Yoshiji Takemoto; Kiyosei Takasu

doi:10.3762/bjoc.8.73

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

Kazato Inanaga, Yu Ogawa, Yuuki Nagamoto, Akihiro Daigaku, Hidetoshi Tokuyama, Yoshiji Takemoto, Kiyosei Takasu

PHA - Molecular Pharmaceutical Science

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

13 Citations (Scopus)

Abstract

A triflic imide (Tf ₂NH) 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, Tf ₂NH catalyzes both of the reactions.

Original language	English
Article number	73
Pages (from-to)	658-661
Number of pages	4
Journal	Beilstein Journal of Organic Chemistry
Volume	8
DOIs	https://doi.org/10.3762/bjoc.8.73
Publication status	Published - 2012 Apr 27

Keywords

Isomerization
One-pot reaction
Organocatalysis
Silyl enol ethers
Triflic imide

Access to Document

10.3762/bjoc.8.73

Cite this

@article{f96e6ff317a34c13bc81c7171afd2a98,

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

abstract = "A triflic imide (Tf 2NH) 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, Tf 2NH catalyzes both of the reactions.",

keywords = "Isomerization, One-pot reaction, Organocatalysis, Silyl enol ethers, Triflic imide",

author = "Kazato Inanaga and Yu Ogawa and Yuuki Nagamoto and Akihiro Daigaku and Hidetoshi Tokuyama and Yoshiji Takemoto and Kiyosei Takasu",

year = "2012",

month = apr,

day = "27",

doi = "10.3762/bjoc.8.73",

language = "English",

volume = "8",

pages = "658--661",

journal = "Beilstein Journal of Organic Chemistry",

issn = "1860-5397",

publisher = "Beilstein-Institut Zur Forderung der Chemischen Wissenschaften",

}

TY - JOUR

T1 - Facile isomerization of silyl enol ethers catalyzed by triflic imide and its application to one-pot isomerization-(2 + 2) cycloaddition

AU - Inanaga, Kazato

AU - Ogawa, Yu

AU - Nagamoto, Yuuki

AU - Daigaku, Akihiro

AU - Tokuyama, Hidetoshi

AU - Takemoto, Yoshiji

AU - Takasu, Kiyosei

PY - 2012/4/27

Y1 - 2012/4/27

N2 - A triflic imide (Tf 2NH) 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, Tf 2NH catalyzes both of the reactions.

AB - A triflic imide (Tf 2NH) 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, Tf 2NH catalyzes both of the reactions.

KW - Isomerization

KW - One-pot reaction

KW - Organocatalysis

KW - Silyl enol ethers

KW - Triflic imide

UR - http://www.scopus.com/inward/record.url?scp=84860620491&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84860620491&partnerID=8YFLogxK

U2 - 10.3762/bjoc.8.73

DO - 10.3762/bjoc.8.73

M3 - Article

AN - SCOPUS:84860620491

SN - 1860-5397

VL - 8

SP - 658

EP - 661

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

M1 - 73

ER -

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

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this