at Google ScholarTitle data
Bringmann, Gerhard ; Breuning, Matthias:
The Atropo-Enantioselective Reduction of Configurationally Unstable Biaryl Hydroxy Aldehydes : A Novel Approach to Axially Chiral Biaryls.
In: Synlett.
(1998)
Issue 6
.
- pp. 634-636.
ISSN 1437-2096
DOI: https://doi.org/10.1055/s-1998-1728
Abstract in another language
The oxazaborolidine-assisted atropo-enantioselective catecholborane reduction of configurationally unstable biaryl hydroxy aldehydes to axially chiral biaryl alcohols by (dynamic) kinetic resolution is achieved in enantiomeric ratios (er) of up to 92:8. Using the same chiral auxiliary, the M- or, optionally, the P-configurated atropisomer can be obtained in good er's - just by variation of the relative quantity of the achiral reductant. This hints at the existence of two competing reaction pathways with opposite asymmetric inductions. The enantiomeric ratios observed strongly depend on the relative steric demand of the substituents ortho to the biaryl axis.
Further data
| Item Type: | Article in a journal |
|---|---|
| Refereed: | Yes |
| Keywords: | atropisomerism; dynamic kinetic resolution; oxazaborolidine; biaryl hydroxy aldehyde; stereoselective biaryl synthesis |
| Institutions of the University: | Faculties Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Professor Organic Chemistry > Professor Organic Chemistry - Univ.-Prof. Dr. Matthias Breuning 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: | No |
| DDC Subjects: | 500 Science 500 Science > 540 Chemistry |
| Date Deposited: | 03 Jul 2017 12:27 |
| Last Modified: | 18 Jul 2023 08:25 |
| URI: | https://eref.uni-bayreuth.de/id/eprint/38240 |