(2+2) Cycloaddition reaction of alkyl enol ethers with acrylates by in situ generated silyl triflic imide catalyst

Kiyosei Takasu; Yuta Miyakawa; Masataka Ihara; Hidetoshi Tokuyama

doi:10.1248/cpb.56.1205

(2+2) Cycloaddition reaction of alkyl enol ethers with acrylates by in situ generated silyl triflic imide catalyst

Kiyosei Takasu, Yuta Miyakawa, Masataka Ihara, Hidetoshi Tokuyama

PHA - Molecular Pharmaceutical Science

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

17 Citations (Scopus)

Abstract

We describe here (2+2) cycloaddition reaction of alkyl enol ethers with acrylates catalyzed by triethylsilyl triflic imide (Et₃SiNTf ₂), which was in situ generated from triethylsilane and triflic imide. The reaction efficiently provides substituted cyclobutanes bearing alkoxy function in a stereoselective manner.

Original language	English
Pages (from-to)	1205-1206
Number of pages	2
Journal	Chemical and Pharmaceutical Bulletin
Volume	56
Issue number	8
DOIs	https://doi.org/10.1248/cpb.56.1205
Publication status	Published - 2008 Aug

Keywords

(2+2) cycloaddition
Cyclobutane
Silane
Triflic imide

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10.1248/cpb.56.1205

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abstract = "We describe here (2+2) cycloaddition reaction of alkyl enol ethers with acrylates catalyzed by triethylsilyl triflic imide (Et3SiNTf 2), which was in situ generated from triethylsilane and triflic imide. The reaction efficiently provides substituted cyclobutanes bearing alkoxy function in a stereoselective manner.",

keywords = "(2+2) cycloaddition, Cyclobutane, Silane, Triflic imide",

author = "Kiyosei Takasu and Yuta Miyakawa and Masataka Ihara and Hidetoshi Tokuyama",

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AU - Takasu, Kiyosei

AU - Miyakawa, Yuta

AU - Ihara, Masataka

AU - Tokuyama, Hidetoshi

PY - 2008/8

Y1 - 2008/8

N2 - We describe here (2+2) cycloaddition reaction of alkyl enol ethers with acrylates catalyzed by triethylsilyl triflic imide (Et3SiNTf 2), which was in situ generated from triethylsilane and triflic imide. The reaction efficiently provides substituted cyclobutanes bearing alkoxy function in a stereoselective manner.

AB - We describe here (2+2) cycloaddition reaction of alkyl enol ethers with acrylates catalyzed by triethylsilyl triflic imide (Et3SiNTf 2), which was in situ generated from triethylsilane and triflic imide. The reaction efficiently provides substituted cyclobutanes bearing alkoxy function in a stereoselective manner.

KW - (2+2) cycloaddition

KW - Cyclobutane

KW - Silane

KW - Triflic imide

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JO - Chemical and Pharmaceutical Bulletin

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(2+2) Cycloaddition reaction of alkyl enol ethers with acrylates by in situ generated silyl triflic imide catalyst

Abstract

Keywords

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