Hierarchically assembled helicates as reaction platform – From stoichiometric Diels-Alder reactions to enamine catalysis

  1. David Van CraenORCID Logo,
  2. Jenny Begall,
  3. Johannes GrosskurthORCID Logo,
  4. Leonard Himmel,
  5. Oliver Linnenberg,
  6. Elisabeth Isaak and
  7. Markus AlbrechtORCID Logo

Submitting author affiliation: RWTH Aachen, Aachen, Germany

Beilstein Arch. 2020, 202082. doi:10.3762/bxiv.2020.82.v1

Published 17 Jul 2020

  • Preprint

Abstract

The stereoselectivity of a Diels-Alder reaction within the periphery of hierarchically assembled titanium(IV) helicates formed from mixtures of achiral, reactive and chiral, unreactive ligands is investigated in detail. Following the pathway of the chiral induction, the chiral ligands, solvents as well as substituents at the dienophile are carefully varied. Based on the results of the stoichiometric reaction a secondary amine catalyzed nitro-Michael reaction is performed as well which affords reasonable diastereoselectivities.

Keywords: hierarchical helicates; remote-control; stereoselectivity; Diels-Alder reaction; enamine catalysis

Supporting Information

Format: DOCX Size: 754.8 KB   Download

How to Cite

When a peer-reviewed version of this preprint is available in the Beilstein Journals, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information:

Van Craen, D.; Begall, J.; Grosskurth, J.; Himmel, L.; Linnenberg, O.; Isaak, E.; Albrecht, M. Beilstein Arch. 2020, 202082. doi:10.3762/bxiv.2020.82.v1

Download Citation
Download RIS (Reference Manager) Download BIB (BIBTEX)

© 2020 Van Craen et al.; licensee Beilstein-Institut.
This is an Open Access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited.
The license is subject to the Beilstein Archives terms and conditions: (https://www.beilstein-archives.org/xiv/terms)

Other Beilstein-Institut Open Science Activities

Logo
Logo
Logo
Symposia