期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 59, 期 27, 页码 10894-10898出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202003673
关键词
anion binding; chiral macrocycles; cooperative asymmetric catalysis; counteranion trapping; supramolecular catalysis
资金
- National Natural Science Foundation of China [21871276, 21502200, 21521002]
- Chinese Academy of Sciences [QYZDJ-SSW-SLH023]
The tight binding enabled by tailor-made macrocycles can be manipulated for tuning the catalysis process. In parallel to well-developed crown ether-based cation-binding catalysis, a macrocycle-enabled counteranion trapping strategy is presented for boosting highly efficient and enantioselective catalysis. A set of bis-diarylthiourea macrocycles containing two BINOL moieties were designed and synthesized. They possess a well-confined chiral cavity and strong binding affinities towards disulfonate anions. Caused by the tight binding, just 1 mol % macrocycle in combination with 1 mol % ethanedisulfonic acid can promote excellent conversion and up to 99 % ee in the Friedel-Crafts reaction of indoles with imines. The acid or the macrocycle alone do not afford any reactivity. The high catalytic efficiency and excellent stereocontrol was ascribed to large, complexation-induced acidity enhancement and tight ion-pairing facilitated by cave-like macrocyclic cavity.
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