The first addition of silyl enol ethers to internal unactivated alkynes

Ken Ichiro Imamura; Eiji Yoshikawa; Vladimir Gevorgyan; Yoshinori Yamamoto

doi:10.1016/S0040-4039(99)00654-1

The first addition of silyl enol ethers to internal unactivated alkynes

Ken Ichiro Imamura, Eiji Yoshikawa, Vladimir Gevorgyan, Yoshinori Yamamoto

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

47 Scopus citations

Abstract

The EtAlCl₂-mediated intramolecular addition of silyl enol ethers to both terminal and internal unactivated alkynes, bearing alkyl and phenyl susbstituents at the alkyne moiety, proceeded exclusively in the endo- fashion to give mono- and bicyclic β,γ-unsaturated ketones in good to excellent yields. The mechanism of this regiospecific Lewis acid-assisted carbocyclization is proposed.

Original language	English (US)
Pages (from-to)	4081-4084
Number of pages	4
Journal	Tetrahedron Letters
Volume	40
Issue number	21
DOIs	https://doi.org/10.1016/S0040-4039(99)00654-1
State	Published - May 21 1999
Externally published	Yes

Keywords

Alkynes
Carbocyclization
Lewis acid
Silyl enol ethers

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(99)00654-1

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title = "The first addition of silyl enol ethers to internal unactivated alkynes",

abstract = "The EtAlCl2-mediated intramolecular addition of silyl enol ethers to both terminal and internal unactivated alkynes, bearing alkyl and phenyl susbstituents at the alkyne moiety, proceeded exclusively in the endo- fashion to give mono- and bicyclic β,γ-unsaturated ketones in good to excellent yields. The mechanism of this regiospecific Lewis acid-assisted carbocyclization is proposed.",

keywords = "Alkynes, Carbocyclization, Lewis acid, Silyl enol ethers",

author = "Imamura, {Ken Ichiro} and Eiji Yoshikawa and Vladimir Gevorgyan and Yoshinori Yamamoto",

year = "1999",

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doi = "10.1016/S0040-4039(99)00654-1",

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T1 - The first addition of silyl enol ethers to internal unactivated alkynes

AU - Imamura, Ken Ichiro

AU - Yoshikawa, Eiji

AU - Gevorgyan, Vladimir

AU - Yamamoto, Yoshinori

PY - 1999/5/21

Y1 - 1999/5/21

N2 - The EtAlCl2-mediated intramolecular addition of silyl enol ethers to both terminal and internal unactivated alkynes, bearing alkyl and phenyl susbstituents at the alkyne moiety, proceeded exclusively in the endo- fashion to give mono- and bicyclic β,γ-unsaturated ketones in good to excellent yields. The mechanism of this regiospecific Lewis acid-assisted carbocyclization is proposed.

AB - The EtAlCl2-mediated intramolecular addition of silyl enol ethers to both terminal and internal unactivated alkynes, bearing alkyl and phenyl susbstituents at the alkyne moiety, proceeded exclusively in the endo- fashion to give mono- and bicyclic β,γ-unsaturated ketones in good to excellent yields. The mechanism of this regiospecific Lewis acid-assisted carbocyclization is proposed.

KW - Alkynes

KW - Carbocyclization

KW - Lewis acid

KW - Silyl enol ethers

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SN - 0040-4039

VL - 40

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 21

ER -

The first addition of silyl enol ethers to internal unactivated alkynes

Abstract

Keywords

ASJC Scopus subject areas

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