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Asymmetric synthesis of (1,5)Naphthalenophanes by Dehydro-Diels-Alder reaction

  • An asymmetric variant of the dehydro-Diels-Alder (DDA) reaction has been developed and applied in the atropselective synthesis of various (1,5)naphthalenophanes. Whereas the suitability of the photochemically induced DDA (PDDA) was limited, the thermally induced DDA provided the desired product, depending on the chiral auxiliary used and the length of the linker, with nearly perfect stereoselectivity. Furthermore, the mechanism of the DDA was investigated by means of DFT calculations, and a stepwise mechanism involving 1,4-biradicals was suggested.

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Metadaten
Author:Pablo WessigORCiDGND, Annika Matthes, Uwe SchildeORCiDGND, Alexandra Kelling
DOI:https://doi.org/10.1002/ejoc.201201594
ISSN:1434-193X (print)
Parent Title (English):European journal of organic chemistry
Publisher:Wiley-VCH
Place of publication:Weinheim
Document Type:Article
Language:English
Year of first Publication:2013
Year of Completion:2013
Release Date:2017/03/26
Tag:Atropisomerism; Chiral auxiliaries; Cyclophanes; Density functional calculations; Macrocycles; Synthetic methods
Issue:11
Pagenumber:7
First Page:2123
Last Page:2129
Funder:Deutsche Forschungsgemeinschaft (DFG) [We-1850/5-1, We-1850/5-3]
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
Peer Review:Referiert