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First example of an atropselective dehydro-Diels-Alder (ADDA) reaction

  • A new concept of a stereoselective synthesis of axially chiral biaryls, formed in the course of the dehydro-Diels-Alder (DDA) reaction, has been disclosed. It is based on asymmetric induction of the newly formed chirality axis by a chirality center, which is present in the two synthesized DDA reactants. Depending on the different length of the linkers joining the alkyne moieties the DDA reaction may be triggered photochemically or thermally, where only the thermal variant was stereoselective.

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Metadaten
Author:Pablo WessigORCiDGND, Charlotte Pick, Uwe SchildeORCiDGND
DOI:https://doi.org/10.1016/j.tetlet.2011.06.024
ISSN:0040-4039 (print)
Parent Title (English):Tetrahedron letters
Publisher:Elsevier
Place of publication:Oxford
Document Type:Article
Language:English
Year of first Publication:2011
Year of Completion:2011
Release Date:2017/03/26
Tag:Alkynes; Atropselecrivity; Biaryls; Cycloaddition; Photochemistry
Volume:52
Issue:32
Pagenumber:3
First Page:4221
Last Page:4223
Funder:Deutsche Forschungsgemeinschaft [We1850-5/1]
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
Peer Review:Referiert