期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2022, 期 38, 页码 -出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202200518
关键词
Asymmetric catalysis; Gold; Chiral counterion; Hydrogen bonding; Ynenones
资金
- European Union [754510]
- European Research Council [835080]
- MCIN/AEI [PID2019-104815GB I00, IJC2019040181-I]
- Severo Ochoa Excellence Accreditation (MIC/AEI) [CEX2019-000925-S]
- MUniv (FPU Fellowship)
- European Research Council (ERC) [835080] Funding Source: European Research Council (ERC)
In this article, the application of H-bonded counterion-directed catalysis to the Au(I)-catalyzed enantioselective tandem cycloisomerization-addition reaction of 2-alkynyl enones was presented. Bicyclic furans were obtained in moderate to excellent yield and enantioselectivity using the optimal catalytic system selected through high-throughput screening. A significant enantioselectivity switch was observed upon addition of the achiral Au(I) component to the Ag(I) salt.
H-bonded counterion-directed catalysis (HCDC) is a strategy wherein a chiral anion that is hydrogen-bonded to the achiral ligand of a metal complex is responsible for enantioinduction. In this article we present the application of H-bonded counterion-directed catalysis to the Au(I)-catalyzed enantioselective tandem cycloisomerization-addition reaction of 2-alkynyl enones. Following the addition of C-, N- or O-centered nucleophiles, bicyclic furans were obtained in moderate to excellent yield and enantioselectivity (28 examples, 59-96 % yield, 62 : 38 to 95 : 5 er). The optimal catalytic system, comprising a phosphinosquaramide Au(I) chloride complex and a BINOL-derived phosphoramidate Ag(I) salt, was selected in a combinatorial fashion from a larger library with the help of high-throughput screening. An enantioselectivity switch of ca. 120 Delta ee% was observed upon addition of the achiral Au(I) component to the Ag(I) salt.
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