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

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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

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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, Advance Article
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, Advance Article , DOI: 10.1039/D0SC00444H

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