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Bidentate Lewis Acid Catalyzed Domino Diels-Alder Reaction of Phthalazine for the Synthesis of Bridged Oligocyclic Tetrahydronaphthalenes

Schweighauser, Luca and Bodoky, Ina and Kessler, Simon N. and Häussinger, Daniel and Donsbach, Carsten and Wegner, Hermann A.. (2016) Bidentate Lewis Acid Catalyzed Domino Diels-Alder Reaction of Phthalazine for the Synthesis of Bridged Oligocyclic Tetrahydronaphthalenes. Organic Letters, 18 (6). pp. 1330-1333.

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Official URL: http://edoc.unibas.ch/51864/

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Abstract

A domino process consisting of an inverse and a normal electron-demand Diels-Alder reaction is presented for the formation of bridged tri- and tetracyclic 1,2,3,4-tetrahydronaphthalenes catalyzed by a bidentate Lewis acid. The products were synthesized in a one-pot reaction from commercially available starting materials and contain up to six stereogenic centers. The tetrahydronaphthalenes were isolated as single diastereomers and are derivatives of phenylethylamine, which is well-known as a scaffold of amphetamine or dopamine.
Faculties and Departments:05 Faculty of Science > Departement Chemie > Chemie > Nuclear Magnetic Resonance (Häussinger)
UniBasel Contributors:Häussinger, Daniel
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:American Chemical Society
ISSN:1523-7060
e-ISSN:1523-7052
Note:Publication type according to Uni Basel Research Database: Journal article
Identification Number:
Last Modified:11 Jan 2017 12:50
Deposited On:11 Jan 2017 12:50

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