Synthesis of cycloalkanone-fused cyclopropanes by Au(I)-catalyzed oxidative ene-yne cyclizations

Yuta Uetake; Takashi Niwa; Masahisa Nakada

doi:10.1016/j.tetlet.2014.10.084

Synthesis of cycloalkanone-fused cyclopropanes by Au(I)-catalyzed oxidative ene-yne cyclizations

Yuta Uetake, Takashi Niwa, Masahisa Nakada^*

^*Corresponding author for this work

School of Advanced Science and Engineering

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

14 Citations (Scopus)

Abstract

Au(I)-catalyzed oxidative cyclizations that successfully convert 1,5-ene-ynes and a 1,6-ene-yne to the corresponding cycloalkanone-fused cyclopropanes are described. This Au(I)-catalyzed oxidative cyclization can be effectively applied to various substrates and is an alternative to the previously used intramolecular cyclopropanation that required potentially explosive diazo compound.

Original language	English
Pages (from-to)	6847-6850
Number of pages	4
Journal	Tetrahedron Letters
Volume	55
Issue number	50
DOIs	https://doi.org/10.1016/j.tetlet.2014.10.084
Publication status	Published - 2014 Dec 10

Keywords

Au(I)-catalysis
Cycloalkanone
Cyclopropane
Ene-yne cyclization
Oxidative cyclization

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2014.10.084

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title = "Synthesis of cycloalkanone-fused cyclopropanes by Au(I)-catalyzed oxidative ene-yne cyclizations",

abstract = "Au(I)-catalyzed oxidative cyclizations that successfully convert 1,5-ene-ynes and a 1,6-ene-yne to the corresponding cycloalkanone-fused cyclopropanes are described. This Au(I)-catalyzed oxidative cyclization can be effectively applied to various substrates and is an alternative to the previously used intramolecular cyclopropanation that required potentially explosive diazo compound.",

keywords = "Au(I)-catalysis, Cycloalkanone, Cyclopropane, Ene-yne cyclization, Oxidative cyclization",

author = "Yuta Uetake and Takashi Niwa and Masahisa Nakada",

note = "Funding Information: This work was financially supported in part by the Grant-in-Aid for Scientific Research on Innovative Areas ( 2105 ) and for Scientific Research (B) ( 25293003 ) by MEXT, and a Waseda University Grant for Special Research Projects. Publisher Copyright: {\textcopyright} 2014 Elsevier Ltd. All rights reserved.",

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doi = "10.1016/j.tetlet.2014.10.084",

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T1 - Synthesis of cycloalkanone-fused cyclopropanes by Au(I)-catalyzed oxidative ene-yne cyclizations

AU - Uetake, Yuta

AU - Niwa, Takashi

AU - Nakada, Masahisa

N1 - Funding Information: This work was financially supported in part by the Grant-in-Aid for Scientific Research on Innovative Areas ( 2105 ) and for Scientific Research (B) ( 25293003 ) by MEXT, and a Waseda University Grant for Special Research Projects. Publisher Copyright: © 2014 Elsevier Ltd. All rights reserved.

PY - 2014/12/10

Y1 - 2014/12/10

N2 - Au(I)-catalyzed oxidative cyclizations that successfully convert 1,5-ene-ynes and a 1,6-ene-yne to the corresponding cycloalkanone-fused cyclopropanes are described. This Au(I)-catalyzed oxidative cyclization can be effectively applied to various substrates and is an alternative to the previously used intramolecular cyclopropanation that required potentially explosive diazo compound.

AB - Au(I)-catalyzed oxidative cyclizations that successfully convert 1,5-ene-ynes and a 1,6-ene-yne to the corresponding cycloalkanone-fused cyclopropanes are described. This Au(I)-catalyzed oxidative cyclization can be effectively applied to various substrates and is an alternative to the previously used intramolecular cyclopropanation that required potentially explosive diazo compound.

KW - Au(I)-catalysis

KW - Cycloalkanone

KW - Cyclopropane

KW - Ene-yne cyclization

KW - Oxidative cyclization

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DO - 10.1016/j.tetlet.2014.10.084

M3 - Article

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SN - 0040-4039

VL - 55

SP - 6847

EP - 6850

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 50

ER -

Synthesis of cycloalkanone-fused cyclopropanes by Au(I)-catalyzed oxidative ene-yne cyclizations

Abstract

Keywords

ASJC Scopus subject areas

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