期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 58, 期 42, 页码 14955-14958出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201908330
关键词
asymmetric catalysis; chirality; molecular machines; rotaxanes; switchable catalysts
资金
- Engineering and Physical Sciences Research Council (EPSRC) [EP/P027067/1]
- EU (European Research Council (ERC)) [786630, 642083]
- European Research Council (ERC) [786630] Funding Source: European Research Council (ERC)
- EPSRC [EP/P027067/1] Funding Source: UKRI
We report on a switchable rotaxane molecular shuttle that features a pseudo-meso 2,5-disubstituted pyrrolidine catalytic unit on the axle whose local symmetry is broken according to the position of a threaded benzylic amide macrocycle. The macrocycle can be selectively switched (with light in one direction; with catalytic acid in the other) with high fidelity between binding sites located to either side of the pyrrolidine unit. The position of the macrocycle dictates the facial bias of the rotaxane-catalyzed conjugate addition of aldehydes to vinyl sulfones. The pseudo-meso non-interlocked thread does not afford significant selectivity as a catalyst (2-14 % ee), whereas the rotaxane affords selectivities of up to 40 % ee with switching of the position of the macrocycle changing the handedness of the product formed (up to 60 % Delta ee).
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