Rhenium(I)-catalyzed cyclization of silyl enol ethers containing a propargyl carboxylate moiety: Versatile access to highly substituted phenols

Kodai Saito; Yuji Onizawa; Hiroyuki Kusama; Nobuharu Iwasawa

doi:10.1002/chem.200903586

Rhenium(I)-catalyzed cyclization of silyl enol ethers containing a propargyl carboxylate moiety: Versatile access to highly substituted phenols

Kodai Saito, Yuji Onizawa, Hiroyuki Kusama, Nobuharu Iwasawa

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

25 Citations (Scopus)

Abstract

Selective migration: The rhenium-catalyzed reaction of 2-siloxy-1-en-5-ynes containing an acyloxy substituent at the propargylic position gave highly substituted phenols in good yields (see scheme). Depending on the structure of the silyl enol ether, either nucleophilic addition of this moiety or 1,2acyloxy migration occurs to give two kinds of synthetically useful, substituted phenols. (Chemical Equation Presented)

Original language	English
Pages (from-to)	4716-4720
Number of pages	5
Journal	Chemistry - A European Journal
Volume	16
Issue number	16
DOIs	https://doi.org/10.1002/chem.200903586
Publication status	Published - 2010 Apr 26
Externally published	Yes

Keywords

Alkynes
Cycloaddition
Elimination
Phenols
Rhenium

ASJC Scopus subject areas

Catalysis
Organic Chemistry

Access to Document

10.1002/chem.200903586

Cite this

@article{92eaeb1cab49445a857b463faecc3f3d,

title = "Rhenium(I)-catalyzed cyclization of silyl enol ethers containing a propargyl carboxylate moiety: Versatile access to highly substituted phenols",

abstract = "Selective migration: The rhenium-catalyzed reaction of 2-siloxy-1-en-5-ynes containing an acyloxy substituent at the propargylic position gave highly substituted phenols in good yields (see scheme). Depending on the structure of the silyl enol ether, either nucleophilic addition of this moiety or 1,2acyloxy migration occurs to give two kinds of synthetically useful, substituted phenols. (Chemical Equation Presented)",

keywords = "Alkynes, Cycloaddition, Elimination, Phenols, Rhenium",

author = "Kodai Saito and Yuji Onizawa and Hiroyuki Kusama and Nobuharu Iwasawa",

year = "2010",

month = apr,

day = "26",

doi = "10.1002/chem.200903586",

language = "English",

volume = "16",

pages = "4716--4720",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "Wiley-VCH Verlag",

number = "16",

}

TY - JOUR

T1 - Rhenium(I)-catalyzed cyclization of silyl enol ethers containing a propargyl carboxylate moiety

T2 - Versatile access to highly substituted phenols

AU - Saito, Kodai

AU - Onizawa, Yuji

AU - Kusama, Hiroyuki

AU - Iwasawa, Nobuharu

PY - 2010/4/26

Y1 - 2010/4/26

N2 - Selective migration: The rhenium-catalyzed reaction of 2-siloxy-1-en-5-ynes containing an acyloxy substituent at the propargylic position gave highly substituted phenols in good yields (see scheme). Depending on the structure of the silyl enol ether, either nucleophilic addition of this moiety or 1,2acyloxy migration occurs to give two kinds of synthetically useful, substituted phenols. (Chemical Equation Presented)

AB - Selective migration: The rhenium-catalyzed reaction of 2-siloxy-1-en-5-ynes containing an acyloxy substituent at the propargylic position gave highly substituted phenols in good yields (see scheme). Depending on the structure of the silyl enol ether, either nucleophilic addition of this moiety or 1,2acyloxy migration occurs to give two kinds of synthetically useful, substituted phenols. (Chemical Equation Presented)

KW - Alkynes

KW - Cycloaddition

KW - Elimination

KW - Phenols

KW - Rhenium

UR - http://www.scopus.com/inward/record.url?scp=77951168752&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=77951168752&partnerID=8YFLogxK

U2 - 10.1002/chem.200903586

DO - 10.1002/chem.200903586

M3 - Article

C2 - 20301146

AN - SCOPUS:77951168752

SN - 0947-6539

VL - 16

SP - 4716

EP - 4720

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 16

ER -

Rhenium(I)-catalyzed cyclization of silyl enol ethers containing a propargyl carboxylate moiety: Versatile access to highly substituted phenols

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this