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.
| Author details: | Pablo WessigORCiDGND, Charlotte Pick, Uwe SchildeORCiDGND |
|---|---|
| DOI: | https://doi.org/10.1016/j.tetlet.2011.06.024 |
| ISSN: | 0040-4039 |
| Title of parent work (English): | Tetrahedron letters |
| Publisher: | Elsevier |
| Place of publishing: | Oxford |
| Publication type: | Article |
| Language: | English |
| Year of first publication: | 2011 |
| Publication year: | 2011 |
| Release date: | 2017/03/26 |
| Tag: | Alkynes; Atropselecrivity; Biaryls; Cycloaddition; Photochemistry |
| Volume: | 52 |
| Issue: | 32 |
| Number of pages: | 3 |
| First page: | 4221 |
| Last Page: | 4223 |
| Funding institution: | Deutsche Forschungsgemeinschaft [We1850-5/1] |
| Organizational units: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie |
| Peer review: | Referiert |
