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Formal Insertion of Thioketenes into Donor-Acceptor Cyclopropanes by Lewis Acid Catalysis

ORCID
0000-0002-6425-2843
Affiliation/Institute
Institute for Organic Chemistry and ‡Institute for Inorganic and Analytical Chemistry, TU Braunschweig , Hagenring 30, 38106 Braunschweig, Germany.
Augustin, André U;
Affiliation/Institute
Institute for Organic Chemistry and ‡Institute for Inorganic and Analytical Chemistry, TU Braunschweig , Hagenring 30, 38106 Braunschweig, Germany.
Busse, Marius;
Affiliation/Institute
Institute for Organic Chemistry and ‡Institute for Inorganic and Analytical Chemistry, TU Braunschweig , Hagenring 30, 38106 Braunschweig, Germany.
Jones, Peter G;
ORCID
0000-0002-3973-2212
Affiliation/Institute
Institute for Organic Chemistry and ‡Institute for Inorganic and Analytical Chemistry, TU Braunschweig , Hagenring 30, 38106 Braunschweig, Germany.
Werz, Daniel B

Donor-acceptor cyclopropanes were reacted under Lewis acid catalysis with 3-thioxocyclobutanones as surrogates for disubstituted thioketenes. A broad scope of 2-substituted tetrahydrothiophenes with a semicyclic double bond was obtained under mild conditions with high functional group tolerance and in excellent yield. A sequence of a formal [3 + 2]-cycloaddition followed by the subsequent release of disubstituted ketene is postulated as the mechanism.

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Original:
Organic letters 20, 3, S. 820 - 823.
(2018)
Date Issued:
2018
URN:
urn:nbn:de:gbv:084-2020022613157
DOI:
10.24355/dbbs.084-202002261308-0
Other identifier (pubmed):
29345137
Language:
English
Type of Resource:
Text
Extent:
4 Seiten
Publisher:
ACS Publications
DDC:
547 Organische Chemie
Location:
Publications of TU Braunschweig
Link to Raw Object:
https://doi.org/10.1021/acs.orglett.7b03961
Hosting institution:
02 - Life Sciences

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License Holder: This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.orglett.7b03961

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