Tetrahedron Letters

, volume 51 , issue 52 , pages 6830-6834

Epoxidation of olefins by β-bromoalkoxydimethylsulfonium ylides

George Majetich ¹

Joel Shimkus ¹

Yang Li ¹

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Department of Chemistry, University of Georgia, Athens, Georgia 30602, USA |

Publication type: Journal Article

Publication date: 2010-12-01

Elsevier

Tetrahedron Letters

scimago Q3

wos Q3

SJR: 0.334

CiteScore: 3.2

Impact factor: 1.5

ISSN: 00404039, 18733581

DOI: 10.1016/j.tetlet.2010.10.068

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Organic Chemistry

Drug Discovery

Biochemistry

Abstract

Olefins can be converted to their respective epoxides in a one-pot procedure by dissolving the olefin in anhydrous DMSO, adding NBS to the reaction mixture to generate a β-bromoalkoxydimethylsulfonium ylide, and then adding DBU to the reaction mixture. A large variety of alkenes were successfully epoxidized with yields largely dependent on the structure of the alkene. Most importantly, the facial selectivity of this one-pot process is the opposite of that observed when using traditional epoxidizing reagents. Electron-poor alkenes are not epoxidized under these conditions.

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Lyssenko Konstantin

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DSc in Chemistry, professor

898 publications, 15 227 citations, 2 reviews

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Lomonosov Moscow State University

National Research University Higher School of Economics

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Majetich G., Shimkus J., Li Y. Epoxidation of olefins by β-bromoalkoxydimethylsulfonium ylides // Tetrahedron Letters. 2010. Vol. 51. No. 52. pp. 6830-6834.

GOST all authors (up to 50) Copy

Majetich G., Shimkus J., Li Y. Epoxidation of olefins by β-bromoalkoxydimethylsulfonium ylides // Tetrahedron Letters. 2010. Vol. 51. No. 52. pp. 6830-6834.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1016/j.tetlet.2010.10.068

UR - https://doi.org/10.1016/j.tetlet.2010.10.068

TI - Epoxidation of olefins by β-bromoalkoxydimethylsulfonium ylides

T2 - Tetrahedron Letters

AU - Majetich, George

AU - Shimkus, Joel

AU - Li, Yang

PY - 2010

DA - 2010/12/01

PB - Elsevier

SP - 6830-6834

IS - 52

VL - 51

SN - 0040-4039

SN - 1873-3581

ER -

BibTex |

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BibTex (up to 50 authors) Copy

@article{2010_Majetich,

author = {George Majetich and Joel Shimkus and Yang Li},

title = {Epoxidation of olefins by β-bromoalkoxydimethylsulfonium ylides},

journal = {Tetrahedron Letters},

year = {2010},

volume = {51},

publisher = {Elsevier},

month = {dec},

url = {https://doi.org/10.1016/j.tetlet.2010.10.068},

number = {52},

pages = {6830--6834},

doi = {10.1016/j.tetlet.2010.10.068}

}

MLA

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MLA Copy

Majetich, George, et al. “Epoxidation of olefins by β-bromoalkoxydimethylsulfonium ylides.” Tetrahedron Letters, vol. 51, no. 52, Dec. 2010, pp. 6830-6834. https://doi.org/10.1016/j.tetlet.2010.10.068.

Publisher

Elsevier

Journal

Tetrahedron Letters

scimago Q3

wos Q3

SJR

0.334

CiteScore

3.2

Impact factor

1.5

ISSN

00404039 (Print)

18733581 (Electronic)