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Evaluation of 5-cis-Substituted Prolinamines as Ligands in Enantioselective, Copper-Catalyzed Henry Reactions

Title data

Kaldun, Johannes ; Prause, Felix ; Scharnagel, Dagmar ; Freitag, Frederik ; Breuning, Matthias:
Evaluation of 5-cis-Substituted Prolinamines as Ligands in Enantioselective, Copper-Catalyzed Henry Reactions.
In: ChemCatChem. Vol. 8 (2016) Issue 10 . - pp. 1846-1856.
ISSN 1867-3899
DOI: https://doi.org/10.1002/cctc.201600240

Abstract in another language

The development of a new catalytic system for enantioselective Henry reactions, which permits superb 99 % ee with a broad variety of aldehydes, is presented. In-depth structure–selectivity investigations with 33 5-cis-substituted prolinamines, prepared from methyl Boc-l-pyroglutamate, revealed that an aromatic or sterically demanding aliphatic substituent in 5-cis position is crucial for high levels of stereocontrol, while bulkier substituents at the nitrogen atoms diminish both, enantioselectivities and reaction rates. The scope of the prime catalyst was expanded to gram-scale and diastereomeric Henry reactions (up to 84:16 dr, 99 % ee). In the course of mechanistic studies, it was proven that the resulting β-nitro alcohols are configurationally stable under the reaction conditions. In addition, competition experiments were used to determine the relative reaction rates of some of the prolinamine-modified catalysts.

Further data

Item Type: Article in a journal
Refereed: Yes
Additional notes: Featured in: Organic Chemistry Highlights, 09.02.2015
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 09:57
Last Modified: 11 Jan 2022 09:57
URI: https://eref.uni-bayreuth.de/id/eprint/68298