Jump to main content
Jump to site search
SCHEDULED MAINTENANCE Close the message box

Maintenance work is planned for Monday 16 August 2021 from 07:00 to 23:59 (BST).

Website performance may be temporarily affected and you may not be able to access some PDFs or images. If this does happen, refreshing your web browser should resolve the issue. We apologise for any inconvenience this might cause and thank you for your patience.


Issue 14, 2020

Enhancing the selectivity of prolinamide organocatalysts using the mechanical bond in [2]rotaxanes

Author affiliations

Abstract

The synthesis of a pair of switchable interlocked prolinamides and their use as organocatalysts in three different enamine-activated processes are reported. A diacylaminopyridine moiety was incorporated into the thread for directing [2]rotaxane formation further allowing the association of complementary small molecules. The rotaxane-based systems were tested as organocatalysts in asymmetric enamine-mediated processes, revealing a significantly improved catalytic ability if compared with the non-interlocked thread. The presence of an electron-withdrawing nitro group at the macrocycle helps to achieve high conversions and enantioselectivities. These systems are able to interact with N-hexylthymine as a cofactor to form supramolecular catalysts displaying a divergent catalytic behaviour. The presence or absence of the cofactor controls the chemoselectivity in competitive reactions.

Graphical abstract: Enhancing the selectivity of prolinamide organocatalysts using the mechanical bond in [2]rotaxanes

Supplementary files

Article information


Submitted
23 Jan 2020
Accepted
10 Mar 2020
First published
11 Mar 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020,11, 3629-3635
Article type
Edge Article

Enhancing the selectivity of prolinamide organocatalysts using the mechanical bond in [2]rotaxanes

M. Calles, J. Puigcerver, D. A. Alonso, M. Alajarin, A. Martinez-Cuezva and J. Berna, Chem. Sci., 2020, 11, 3629 DOI: 10.1039/D0SC00444H

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

Read more about how to correctly acknowledge RSC content.


Social activity

Search articles by author

Spotlight

Advertisements