O'Toole, Sarah E. and Rose, Christopher A. and Gundala, Sivaji and Zeitler, Kirsten and Connon, Stephen J. (2011) Highly Chemoselective Direct Crossed Aliphatic-Aromatic Acyloin Condensations with Triazolium-Derived Carbene Catalysts. JOURNAL OF ORGANIC CHEMISTRY, 76 (2). pp. 347-357. ISSN 0022-3263,
Full text not available from this repository. (Request a copy)Abstract
It has been shown for the first time that-triazolium precatalysts promote (in the presence of base) highly chemoselective crossed acyloin condensation reactions between aliphatic and ortho-substituted aromatic aldehydes. An o-bromine atom can serve as a temporary directing group to ensure high chemoselectivity (regardless of the nature of the other substituents on the aromatic ring) which then can be conveniently removed. The process is of broad scope and is operationally simple as it does not require the preactivation of any of the coupling partners to ensure selectivtiy. Preliminary data indicate that highly enantioselective variants of the reaction are feasible using chiral precatalysts.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | ALPHA-HYDROXY-KETONES; N-HETEROCYCLIC CARBENES; CARBON BOND FORMATIONS; BENZOIN CONDENSATION; ASYMMETRIC-SYNTHESIS; ANION EQUIVALENTS; ENANTIOSELECTIVE SYNTHESIS; NUCLEOPHILIC ACYLATION; LANTHANUM TRICYANIDE; THIAZOLIUM SALT; |
| 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: | 29 Jun 2020 05:32 |
| Last Modified: | 29 Jun 2020 05:32 |
| URI: | https://pred.uni-regensburg.de/id/eprint/21383 |
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