Economy of catalyst synthesis—convenient access to libraries of Di- and tetranaphtho azepinium compounds

3Citations
Citations of this article
8Readers
Mendeley users who have this article in their library.

Abstract

Efficient optimization procedures in chiral catalysis are usually linked to a straightforward strategy to access groups of structurally similar catalysts required for fine-tuning. The ease of building up such ligand libraries can be increased when the structure-modifying step (introduction of a substituent) is done at a later stage of the synthesis. This is demonstrated for the extended family of di- and tetranaphtho azepinium compounds, widely used as chiral phase transfer catalysts (PTC). Using 2,6-diiodo-4,5-dihydro-3H-dinaphtho[2,1-c:1,2-e]azepine and 4,8-diiodo-6,7-dihydro-5H-dibenzo[c,e]azepine, respectively, as key intermediates, 18 spiro-azepinium compounds were synthesized in a total yield of 25–42% over 6–7 steps from 1,1-binaphthyl-2,2-dicarboxylic acid or diphenic acid, respectively. The replacement of iodo groups with aryl substituents was performed as the last or the penultimate step of the synthesis.

Cite

CITATION STYLE

APA

Tharamak, S., Knittl-Frank, C., Manaprasertsak, A., Pengsook, A., Suchy, L., Schuller, P., … Widhalm, M. (2018). Economy of catalyst synthesis—convenient access to libraries of Di- and tetranaphtho azepinium compounds. Molecules, 23(4). https://doi.org/10.3390/molecules23040750

Register to see more suggestions

Mendeley helps you to discover research relevant for your work.

Already have an account?

Save time finding and organizing research with Mendeley

Sign up for free