2026-04-13T02:09:36Zhttps://recercat.cat/oai/requestoai:recercat.cat:2072/5227262024-12-20T20:40:58Zcom_2072_300912com_2072_4427col_2072_301309
RECERCAT
author
Martí, Àlex
author
Montesinos-Magraner, Marc
author
Echavarren, Antonio M.
author
Franchino, Allegra
2022-09-29T14:47:03Z2024-04-23T10:57:55Z
2022-09-29T14:47:03Z2024-04-23T10:57:55Z
2022-06-23
http://hdl.handle.net/2072/522726
https://doi.org/10.1002/ejoc.202200518
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 Δee% was observed upon addition of the achiral Au(I)
component to the Ag(I) salt.
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H-Bonded Counterion-Directed Catalysis: Enantioselective Gold(I)-Catalyzed Addition to 2-Alkynyl Enones as a Case Study
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