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

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Title: Enhancing the selectivity of prolinamide organocatalysts using the mechanical bond in [2]rotaxanes
Authors: Calles, María | Puigcerver, Julio | Alonso, Diego A. | Alajarin, Mateo | Martinez-Cuezva, Alberto | Berna, Jose
Research Group/s: Catálisis Estereoselectiva en Síntesis Orgánica (CESO)
Center, Department or Service: Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica
Keywords: Prolinamide | Organocatalysts | Mechanical bond | [2]rotaxanes
Knowledge Area: Química Orgánica
Issue Date: 11-Mar-2020
Publisher: Royal Society of Chemistry
Citation: Chemical Science. 2020, 11: 3629-3635. doi:10.1039/d0sc00444h
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.
Sponsor: This work was supported by the MINECO and MICINN (CTQ2017-87231-P, RYC-2017-22700 and PGC2018-096616-BI00) with joint financing by FEDER Funds and Fundación Seneca-CARM (Project 20811/PI/18). D. A. A. also thanks the University of Alicante for the financial support (VIGROB-173FI).
URI: http://hdl.handle.net/10045/105267
ISSN: 2041-6520 (Print) | 2041-6539 (Online)
DOI: 10.1039/d0sc00444h
Language: eng
Type: info:eu-repo/semantics/article
Rights: This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Peer Review: si
Publisher version: https://doi.org/10.1039/d0sc00444h
Appears in Collections:INV - CESO - Artículos de Revistas

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