Organic Letters, volume 21, issue 23, pages 9405-9409

(4 + 3)-Cycloaddition of Donor–Acceptor Cyclopropanes with Thiochalcones: A Diastereoselective Access to Tetrahydrothiepines

André U Augustin ¹

J Luca Merz ¹

Peter G. Jones ¹

Grzegorz Mloston ²

Daniel B. Werz ¹

Hide authors affiliations Show authors affiliations: 2 affiliations

Technische Universität Braunschweig, Institute of Organic Chemistry and Institute of Inorganic and Analytical Chemistry, Hagenring 30, 38106 Braunschweig, Germany |

Department of Organic and Applied Chemistry, University of Łodź, Tamka 12, 91-403 Łodź, Poland |

Publication type: Journal Article

Publication date: 2019-11-11

American Chemical Society (ACS)

Journal: Organic Letters

SJR: 1.245

CiteScore: 9.3

Impact factor: 4.9

ISSN: 15237060, 15237052

DOI: 10.1021/acs.orglett.9b03623

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Organic Chemistry

Biochemistry

Physical and Theoretical Chemistry

Abstract

A general approach is described for the formation of tetrahydrothiepines using donor-acceptor cyclopropanes. Thiochalcones, functioning as sulfur-containing four-atom building blocks, were reacted in a Lewis acid catalyzed formal (4 + 3)-cycloaddition reaction with donor-acceptor cyclopropanes as three-atom building blocks. Under mild conditions various tetrahydrothiepines were synthesized in good yields in a stereospecific reaction with high functional group tolerance.

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GOST Copy

Augustin A. U. et al. (4 + 3)-Cycloaddition of Donor–Acceptor Cyclopropanes with Thiochalcones: A Diastereoselective Access to Tetrahydrothiepines // Organic Letters. 2019. Vol. 21. No. 23. pp. 9405-9409.

GOST all authors (up to 50) Copy

Augustin A. U., Merz J. L., Jones P. G., Mloston G., Werz D. B. (4 + 3)-Cycloaddition of Donor–Acceptor Cyclopropanes with Thiochalcones: A Diastereoselective Access to Tetrahydrothiepines // Organic Letters. 2019. Vol. 21. No. 23. pp. 9405-9409.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1021/acs.orglett.9b03623

UR - https://doi.org/10.1021/acs.orglett.9b03623

TI - (4 + 3)-Cycloaddition of Donor–Acceptor Cyclopropanes with Thiochalcones: A Diastereoselective Access to Tetrahydrothiepines

T2 - Organic Letters

AU - Augustin, André U

AU - Merz, J Luca

AU - Jones, Peter G.

AU - Mloston, Grzegorz

AU - Werz, Daniel B.

PY - 2019

DA - 2019/11/11

PB - American Chemical Society (ACS)

SP - 9405-9409

IS - 23

VL - 21

SN - 1523-7060

SN - 1523-7052

ER -

BibTex |

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BibTex (up to 50 authors) Copy

@article{2019_Augustin,

author = {André U Augustin and J Luca Merz and Peter G. Jones and Grzegorz Mloston and Daniel B. Werz},

title = {(4 + 3)-Cycloaddition of Donor–Acceptor Cyclopropanes with Thiochalcones: A Diastereoselective Access to Tetrahydrothiepines},

journal = {Organic Letters},

year = {2019},

volume = {21},

publisher = {American Chemical Society (ACS)},

month = {nov},

url = {https://doi.org/10.1021/acs.orglett.9b03623},

number = {23},

pages = {9405--9409},

doi = {10.1021/acs.orglett.9b03623}

}

MLA

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MLA Copy

Augustin, André U., et al. “(4 + 3)-Cycloaddition of Donor–Acceptor Cyclopropanes with Thiochalcones: A Diastereoselective Access to Tetrahydrothiepines.” Organic Letters, vol. 21, no. 23, Nov. 2019, pp. 9405-9409. https://doi.org/10.1021/acs.orglett.9b03623.

Found error?

Publisher

American Chemical Society (ACS)

Journal

Organic Letters

SJR

1.245

CiteScore

9.3

Impact factor

4.9

ISSN

15237060 (Print)

15237052 (Electronic)