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Host-Catalyzed Cyclodehydration–Rearrangement Cascade Reaction of Unsaturated Tertiary Alcohols

Catti, Lorenzo and Pöthig, Alexander and Tiefenbacher, Konrad. (2017) Host-Catalyzed Cyclodehydration–Rearrangement Cascade Reaction of Unsaturated Tertiary Alcohols. Advanced Synthesis and Catalysis, 359 (8). pp. 1331-1338.

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Official URL: http://edoc.unibas.ch/58945/

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Abstract

The Brønsted acidic resorcin[4]arene hexamer can be applied as an effective catalyst in the dehydrative cyclization and subsequent rearrangement of unsaturated tertiary alcohols. This is the first report on catalyzing such a reaction with a Brønsted acid. Scope and limitations of this cyclopentene-forming reaction sequence are presented. Furthermore, substrate-selective conversion as well as competitive inhibition are described and provide evidence that the reactions proceed within the cavity of the self-assembled structure. Additionally, a cyclobutanone-forming intramolecular hydride transfer of an encapsulated cyclopropyl acetate is reported.
Faculties and Departments:05 Faculty of Science > Departement Chemie
05 Faculty of Science > Departement Chemie > Chemie > Synthesis of Functional Modules (Tiefenbacher)
UniBasel Contributors:Tiefenbacher, Konrad Karl and Catti, Lorenzo
Item Type:Article, refereed
Article Subtype:Further Journal Contribution
Publisher:Wiley
ISSN:1615-4150
e-ISSN:1615-4169
Note:Publication type according to Uni Basel Research Database: Journal item
Identification Number:
Last Modified:17 Jan 2018 11:19
Deposited On:17 Jan 2018 11:18

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