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  Taming of Furfurylidenes by Chiral Bismuth-Rhodium Paddlewheel Catalysts. Preparation and Functionalization of Optically Active 1,1-Disubstituted (Trifluoromethyl)cyclopropanes

Peeters, M., Decaens, J., & Fürstner, A. (2023). Taming of Furfurylidenes by Chiral Bismuth-Rhodium Paddlewheel Catalysts. Preparation and Functionalization of Optically Active 1,1-Disubstituted (Trifluoromethyl)cyclopropanes. Angewandte Chemie International Edition, 62(44): e202311598. doi:10.1002/anie.202311598.

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443_anie202311598-s1-si_cf3-cyclopropanes_v2.pdf (Supplementary material), 8MB
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443_anie202311598-s1-si_cf3-cyclopropanes_v2.pdf
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 Creators:
Peeters, Matthias1, Author           
Decaens, Jonathan1, Author           
Fürstner, Alois1, Author           
Affiliations:
1Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445584              

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Free keywords: Asymmetric Catalysis; Bioisosteres; Cyclopropanation; Heterobimetallic Complexes; Rhodium Carbenes
 Abstract: Although 2-furyl-carbenes (furfurylidenes) are prone to instantaneous electrocyclic ring opening, chiral [BiRh]-paddlewheel complexes empowered by London dispersion allow (trifluoromethyl)furfurylidene metal complexes to be generated from a bench-stable triftosylhydrazone precursor. These reactive intermediates engage in asymmetric [2+1] cycloadditions and hence open entry into valuable trifluoromethylated cyclopropane or −cyclopropene in optically active form, which are important building blocks for medicinal chemistry but difficult to make otherwise.

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Language(s): eng - English
 Dates: 2023-08-092023-09-122023-10-26
 Publication Status: Issued
 Pages: 6
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/anie.202311598
 Degree: -

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Title: Angewandte Chemie International Edition
  Abbreviation : Angew. Chem. Int. Ed.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 62 (44) Sequence Number: e202311598 Start / End Page: - Identifier: ISSN: 1433-7851
CoNE: https://pure.mpg.de/cone/journals/resource/1433-7851