Spectral study of specific interactions between zwitterionic compounds and protic solvents

Babusca, Daniela; Morosanu, Cezarina; Dorohoi, Dana Ortansa

doi:10.1016/j.saa.2016.04.034

Cited by 8 publications

(1 citation statement)

References 17 publications

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“…When the gold atom sitting in the cavity was now cationic, we found five molecules of methanol around it, one of them interacting directly with the metallic center. It is also known from the literature that in a binary solution of solvents which differ in their polarity and their protic properties (here CH 2 Cl 2 and ROH), the statistical average weight of the protic solvent in the first solvation shell of a cation will be higher than that in the bulk mixture . Thus, after addition of the substrate in dichloromethane, assuming that the interaction of the cationic gold species with CH 2 Cl 2 is weak, ROH molecules would remain close to the carbene intermediate B , leading to the formation of 4 .…”

Section: Resultsmentioning

confidence: 99%

β-Cyclodextrin–NHC–Gold(I) Complex (β-ICyD)AuCl: A Chiral Nanoreactor for Enantioselective and Substrate-Selective Alkoxycyclization Reactions

et al. 2020

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NHC-capped β-cyclodextrin (β-ICyD) was used as a ligand for gold-catalyzed alkoxycyclization reactions. The cavity was found to be responsible for a triple selectivity: (i) the asymmetric shape of the cavity of β-ICyD induced highly stereoselective cyclizations, (ii) the shape of the interior favored the formation of a six-membered ring in the absence of a nucleophile, and finally, (iii) the encapsulation of the metal inside the cavity disfavored the addition of sterically hindered alcohols. Highly enantioselective and substrate-selective alkoxycyclizations of enynes are therefore promoted by the cavity-based molecular reactor (β-ICyD)AuCl.

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Section: Resultsmentioning

confidence: 99%