Interlocking the Catalyst: Thread versus Rotaxane-Mediated Enantiodivergent Michael Addition of Ketones to β-Nitrostyrene

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Title: Interlocking the Catalyst: Thread versus Rotaxane-Mediated Enantiodivergent Michael Addition of Ketones to β-Nitrostyrene
Authors: Martinez-Cuezva, Alberto | Marin-Luna, Marta | Alonso, Diego A. | Ros Ñíguez, Diego | Alajarin, Mateo | 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: Catalyst | Rotaxanes | Ketones | Enantioselective Michael addition | β-nitrostyrene
Knowledge Area: Química Orgánica
Issue Date: 19-Jun-2019
Publisher: American Chemical Society
Citation: Organic Letters. 2019, 21(13): 5192-5196. doi:10.1021/acs.orglett.9b01791
Abstract: Fumaramide threads bearing one l-prolinamide fragment have been designed as templates for promoting the efficient formation of novel Leigh’s [2]rotaxanes. Both threads and rotaxanes are shown to catalyze the asymmetric addition of ketones to β-nitrostyrene in an enantio- and diastereoselective manner. Interestingly, the enantioselective course of these processes is reversed simply by changing from thread to rotaxane as catalyst. DFT computations have allowed to rationalize the stereodivergence shown by the interlocked and noninterlocked catalysts.
Sponsor: This work was supported by the MINECO (CTQ2017-87231-P and CTQ2015-66624-P) with joint financing by FEDER Funds and Fundación Seneca-CARM (Project 20811/PI/18). A.M.-C. thanks MICINN for a Ramon y Cajal contract and funding (RYC-2017-22700). M.M.L. thanks Xunta de Galicia for her postdoctoral contract (ED418B 2016/166-0).
URI: http://hdl.handle.net/10045/94129
ISSN: 1523-7060 (Print) | 1523-7052 (Online)
DOI: 10.1021/acs.orglett.9b01791
Language: eng
Type: info:eu-repo/semantics/article
Rights: © 2019 American Chemical Society
Peer Review: si
Publisher version: https://doi.org/10.1021/acs.orglett.9b01791
Appears in Collections:INV - CESO - Artículos de Revistas

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