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Enantioselective addition of diethylzinc to aldehydes catalyzed by 5-cis-substituted proline derivatives

Title 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
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