at Google ScholarTitle data
Prause, Felix ; Wagner, Stefan ; Breuning, Matthias:
Enantioselective addition of diethylzinc to aldehydes catalyzed by 5-cis-substituted proline derivatives.
In: Tetrahedron.
Vol. 75
(2019)
Issue 1
.
- pp. 94-101.
ISSN 0040-4020
DOI: https://doi.org/10.1016/j.tet.2018.11.030
Abstract in another language
5-Cis-substituted prolinols, prolinamines, and prolinamine sulfonamides proved to be efficient ligands for the enantioselective addition of diethylzinc to aldehydes, providing up to 99% ee. The sense of asymmetric induction can be controlled by the nature of the exocyclic functional group (CPh2OH vs. CH2NHR vs. CH2NHSO3R). The additional 5-cis substituent exerts a strong beneficial effect on the chirality transfer since it rigidifies the catalyst structure. The stereochemical outcome of the reactions is discussed in detail on the respective transition states.
Further data
| Item Type: | Article in a journal |
|---|---|
| Refereed: | Yes |
| Keywords: | Enantioselective catalysis; Chiral ligands; Pyrrolidine; Diethylzinc; Asymmetric addition |
| Institutions of the University: | Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Professor Organic Chemistry > Professor Organic Chemistry - Univ.-Prof. Dr. Matthias Breuning Faculties Faculties > Faculty of Biology, Chemistry and Earth Sciences Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Professor Organic Chemistry |
| Result of work at the UBT: | Yes |
| DDC Subjects: | 500 Science > 540 Chemistry |
| Date Deposited: | 11 Jan 2022 08:12 |
| Last Modified: | 11 Jan 2022 08:12 |
| URI: | https://eref.uni-bayreuth.de/id/eprint/68293 |