Stereospecific Reaction of Donor-Acceptor Cyclopropanes with
Thioketones: A Novel Access to Highly Substituted Tetrahydrothiophenes

Augustin, André, U.; Sensse, Maximilian; Jones, Peter, G.; Werz, Daniel, B.

doi:10.24355/dbbs.084-201808101131-0

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Stereospecific Reaction of Donor-Acceptor Cyclopropanes with Thioketones : A Novel Access to Highly Substituted Tetrahydrothiophenes

Augustin, André U.; Sensse, Maximilian ; Jones, Peter G.; Werz, Daniel B.

Lewis-acid-catalyzed reactions of 2-substituted cyclopropane 1,1-dicarboxylates with thioketones are described. Highly substituted tetrahydrothiophenes with two adjacent quaternary carbon atoms were obtained in a stereospecific manner under mild conditions and in high yield using AlCl3 as Lewis acid. Moreover, an intramolecular approach was successfully implemented to gain access to sulfur-bridged [n.2.1] bicyclic ring systems. Conversion of selenoketones, the heavier analogs, under similar conditions resulted in the formation of various tetrahydroselenophenes.

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Original:: Angew. Chem. Int.Ed. 2017, 56, Issue45, DOI: 10.1002/anie.201708346
Date Issued:: 2017
URN:: urn:nbn:de:gbv:084-2018081314195
DOI:: 10.24355/dbbs.084-201808101131-0
PPN:: 1028857713
Language:: English
Type of Resource:: Text
Extent:: 5 Seiten
Project name:: Gain by Strain: Precise Cuts of Cyclopropanes as Key to Molecular Complexity
Project Acronym:: GAINBYSTRAIN
Grant ID:: 648711
Program-ID:: H2020
Organization-ID:: EC
DDC:: 540 Chemie
Location:: Publications of TU Braunschweig
URL:: https://doi.org/10.1002/anie.201708346
URL:: https://onlinelibrary.wiley.com/doi/full/10.1002/anie.201708346
Hosting institution:: 02 - Life Sciences
Comment:: Dedicated to Professor Stefan Schulz on the occasion of his 60th birthday.
Comment:: "This is the peer reviewed version of the following article: Augustin, André / Sensse, Maximilian / Jones, Peter / et al: Stereospecific Reaction of Donor-Acceptor Cyclopropanes with Thioketones. A Novel Access to Highly Substituted Tetrahydrothiophenes., which has been published in final form at Angew. Chem. Int.Ed. 2017, 56, Issue45, https://doi.org/10.1002/anie.201708346. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions."