Organic Letters

, volume 14 , issue 3 , pages 712-715

Halonium-Initiated C–O Bond Formation via Umpolung of α-Carbon to the Carbonyl: Efficient Access to 5-Amino-3(2H)-furanones

Ying Wei ¹

Shaoxia Lin ¹

Hongxun Xue ¹

F.S. Liang ¹

BAOZHONG ZHAO ¹

Hide authors affiliations Show authors affiliations: 1 affiliation

Department of Chemistry, Northeast Normal University, Changchun 130024, China |

Publication type: Journal Article

Publication date: 2012-01-24

American Chemical Society (ACS)

Organic Letters

scimago Q1

wos Q1

SJR: 1.235

CiteScore: 8.7

Impact factor: 5.0

ISSN: 15237060, 15237052

DOI: 10.1021/ol203183k

Copy DOI

PubMed ID: 22273111

Organic Chemistry

Biochemistry

Physical and Theoretical Chemistry

Abstract

Highly efficient C-O bond formation has been developed via carboxylic acid catalyzed reaction of 1-acetylcyclopropanecarboxamides with N-halosuccinimide (NXS), which provides strategically novel and atom-economic access to biologically important 5-amino-3(2H)-furanones. The mechanism of halonium-initiated tandem oxa-cyclization and ring opening of cyclopropane was proposed. A variety of nucleophiles were found to open the cyclopropane.

Found

1 citation

Vereshchagin Anatoly

DSc in Chemistry

163 publications, 2 730 citations, 8 reviews

h-index: 28

N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

Top-30

Journals

	1 2 3 4 5
Organic Letters	Organic Letters, 5, 11.9% Organic Letters 5 publications, 11.9%
Journal of Organic Chemistry	Journal of Organic Chemistry, 5, 11.9% Journal of Organic Chemistry 5 publications, 11.9%
Organic and Biomolecular Chemistry	Organic and Biomolecular Chemistry, 5, 11.9% Organic and Biomolecular Chemistry 5 publications, 11.9%
Advanced Synthesis and Catalysis	Advanced Synthesis and Catalysis, 3, 7.14% Advanced Synthesis and Catalysis 3 publications, 7.14%
RSC Advances	RSC Advances, 3, 7.14% RSC Advances 3 publications, 7.14%
Mendeleev Communications	Mendeleev Communications, 2, 4.76% Mendeleev Communications 2 publications, 4.76%
Nature Communications	Nature Communications, 1, 2.38% Nature Communications 1 publication, 2.38%
Monatshefte fur Chemie	Monatshefte fur Chemie, 1, 2.38% Monatshefte fur Chemie 1 publication, 2.38%
Tetrahedron	Tetrahedron, 1, 2.38% Tetrahedron 1 publication, 2.38%
ChemistrySelect	ChemistrySelect, 1, 2.38% ChemistrySelect 1 publication, 2.38%
Angewandte Chemie	Angewandte Chemie, 1, 2.38% Angewandte Chemie 1 publication, 2.38%
Angewandte Chemie - International Edition	Angewandte Chemie - International Edition, 1, 2.38% Angewandte Chemie - International Edition 1 publication, 2.38%
Chemical Record	Chemical Record, 1, 2.38% Chemical Record 1 publication, 2.38%
ChemInform	ChemInform, 1, 2.38% ChemInform 1 publication, 2.38%
Chemistry - A European Journal	Chemistry - A European Journal, 1, 2.38% Chemistry - A European Journal 1 publication, 2.38%
Chemical Reviews	Chemical Reviews, 1, 2.38% Chemical Reviews 1 publication, 2.38%
Chemical Communications	Chemical Communications, 1, 2.38% Chemical Communications 1 publication, 2.38%
Green Chemistry	Green Chemistry, 1, 2.38% Green Chemistry 1 publication, 2.38%
Synthetic Communications	Synthetic Communications, 1, 2.38% Synthetic Communications 1 publication, 2.38%
Synlett	Synlett, 1, 2.38% Synlett 1 publication, 2.38%
Synthesis	Synthesis, 1, 2.38% Synthesis 1 publication, 2.38%
Chemistry of Heterocyclic Compounds	Chemistry of Heterocyclic Compounds, 1, 2.38% Chemistry of Heterocyclic Compounds 1 publication, 2.38%
	1 2 3 4 5

Publishers

	2 4 6 8 10 12
Wiley	Wiley, 11, 26.19% Wiley 11 publications, 26.19%
American Chemical Society (ACS)	American Chemical Society (ACS), 11, 26.19% American Chemical Society (ACS) 11 publications, 26.19%
Royal Society of Chemistry (RSC)	Royal Society of Chemistry (RSC), 10, 23.81% Royal Society of Chemistry (RSC) 10 publications, 23.81%
Springer Nature	Springer Nature, 3, 7.14% Springer Nature 3 publications, 7.14%
Elsevier	Elsevier, 2, 4.76% Elsevier 2 publications, 4.76%
OOO Zhurnal "Mendeleevskie Soobshcheniya"	OOO Zhurnal "Mendeleevskie Soobshcheniya", 2, 4.76% OOO Zhurnal "Mendeleevskie Soobshcheniya" 2 publications, 4.76%
Georg Thieme Verlag KG	Georg Thieme Verlag KG, 2, 4.76% Georg Thieme Verlag KG 2 publications, 4.76%
Taylor & Francis	Taylor & Francis, 1, 2.38% Taylor & Francis 1 publication, 2.38%
	2 4 6 8 10 12

We do not take into account publications without a DOI.
Statistics recalculated weekly.

Are you a researcher?

Create a profile to get free access to personal recommendations for colleagues and new articles.

Metrics

Cite this

GOST |

Cite this

GOST Copy

Wei Y. et al. Halonium-Initiated C–O Bond Formation via Umpolung of α-Carbon to the Carbonyl: Efficient Access to 5-Amino-3(2H)-furanones // Organic Letters. 2012. Vol. 14. No. 3. pp. 712-715.

GOST all authors (up to 50) Copy

Wei Y., Lin S., Xue H., Liang F., ZHAO B. Halonium-Initiated C–O Bond Formation via Umpolung of α-Carbon to the Carbonyl: Efficient Access to 5-Amino-3(2H)-furanones // Organic Letters. 2012. Vol. 14. No. 3. pp. 712-715.

RIS |

Cite this

RIS Copy

TY - JOUR

DO - 10.1021/ol203183k

UR - https://doi.org/10.1021/ol203183k

TI - Halonium-Initiated C–O Bond Formation via Umpolung of α-Carbon to the Carbonyl: Efficient Access to 5-Amino-3(2H)-furanones

T2 - Organic Letters

AU - Wei, Ying

AU - Lin, Shaoxia

AU - Xue, Hongxun

AU - Liang, F.S.

AU - ZHAO, BAOZHONG

PY - 2012

DA - 2012/01/24

PB - American Chemical Society (ACS)

SP - 712-715

IS - 3

VL - 14

PMID - 22273111

SN - 1523-7060

SN - 1523-7052

ER -

BibTex |

Cite this

BibTex (up to 50 authors) Copy

@article{2012_Wei,

author = {Ying Wei and Shaoxia Lin and Hongxun Xue and F.S. Liang and BAOZHONG ZHAO},

title = {Halonium-Initiated C–O Bond Formation via Umpolung of α-Carbon to the Carbonyl: Efficient Access to 5-Amino-3(2H)-furanones},

journal = {Organic Letters},

year = {2012},

volume = {14},

publisher = {American Chemical Society (ACS)},

month = {jan},

url = {https://doi.org/10.1021/ol203183k},

number = {3},

pages = {712--715},

doi = {10.1021/ol203183k}

}

MLA

Cite this

MLA Copy

Wei, Ying, et al. “Halonium-Initiated C–O Bond Formation via Umpolung of α-Carbon to the Carbonyl: Efficient Access to 5-Amino-3(2H)-furanones.” Organic Letters, vol. 14, no. 3, Jan. 2012, pp. 712-715. https://doi.org/10.1021/ol203183k.

Publisher

American Chemical Society (ACS)

Journal

Organic Letters

scimago Q1

wos Q1

SJR

1.235

CiteScore

8.7

Impact factor

5.0

ISSN

15237060 (Print)

15237052 (Electronic)