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.
| Author details: | Pablo WessigORCiDGND, Annika Matthes, Uwe SchildeORCiDGND, Alexandra Kelling |
|---|---|
| DOI: | https://doi.org/10.1002/ejoc.201201594 |
| ISSN: | 1434-193X |
| Title of parent work (English): | European journal of organic chemistry |
| Publisher: | Wiley-VCH |
| Place of publishing: | Weinheim |
| Publication type: | Article |
| Language: | English |
| Year of first publication: | 2013 |
| Publication year: | 2013 |
| Release date: | 2017/03/26 |
| Tag: | Atropisomerism; Chiral auxiliaries; Cyclophanes; Density functional calculations; Macrocycles; Synthetic methods |
| Issue: | 11 |
| Number of pages: | 7 |
| First page: | 2123 |
| Last Page: | 2129 |
| Funding institution: | Deutsche Forschungsgemeinschaft (DFG) [We-1850/5-1, We-1850/5-3] |
| Organizational units: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie |
| Peer review: | Referiert |
