Rose, Christopher A. and Gundala, Sivaji and Fagan, Claire-Louise and Franz, Johannes F. and Connon, Stephen J. and Zeitler, Kirsten (2012) NHC-catalysed, chemoselective crossed-acyloin reactions. CHEMICAL SCIENCE, 3 (3). pp. 735-740. ISSN 2041-6520, 2041-6539
Full text not available from this repository. (Request a copy)Abstract
It has been shown for the first time that relatively electron deficient triazolium pre-catalysts promote (at low loadings in the presence of base) highly chemoselective crossed acyloin condensation reactions between aldehydes and alpha-ketoesters to afford densely functionalized products incorporating a quaternary stereocentre of considerable synthetic potential. Hydroacylation pathways which have hitherto been dominant in these reactions can be completely avoided. The scope of the process is extraordinarily broad with respect to both coupling partners, and a preliminary study has established the principle that a high degree of stereochemical control over the reaction can also be exercised via the use of a chiral NHC precursor. It has also been shown for the first time that coupling of benzyl alpha-ketoesters with aldehydes followed by acylation and simple hydrogenolysis furnishes a product formally derived from the chemoselective 1 : 1 coupling of two different aliphatic aldehydes in high yield with absolute control over which coupling partner behaves as the acyl-anion equivalent.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | N-HETEROCYCLIC CARBENES; KETONE BENZOIN REACTIONS; ASYMMETRIC-SYNTHESIS; MOLECULAR-OXYGEN; 1,3-DICARBONYL COMPOUNDS; ACETOLACTATE SYNTHASE; ABSOLUTE-CONFIGURATION; ALPHA-HYDROXYLATION; ACTIVATED KETONES; FORMING REACTIONS; |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Alumni or Retired Professors > Arbeitskreis Dr. Kirsten Zeitler |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 25 May 2020 08:58 |
| Last Modified: | 25 May 2020 08:58 |
| URI: | https://pred.uni-regensburg.de/id/eprint/19550 |
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