期刊
CHEMICAL SCIENCE
卷 11, 期 14, 页码 3629-3635出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0sc00444h
关键词
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资金
- MINECO [CTQ2017-87231-P, RYC-2017-22700, PGC2018-096616-BI00]
- MICINN [CTQ2017-87231-P, RYC-2017-22700, PGC2018-096616-BI00]
- FEDER Funds [20811/PI/18]
- Fundacion Seneca-CARM [20811/PI/18]
- University of Alicante [VIGROB-173FI]
- Centro de Computacion Cientifica-UAM [RES-QSB-2019-3-0012]
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.
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