162136-06-3Relevant articles and documents
Scalable Biomimetic Syntheses of Paeciloketal B, 1- epi-Paeciloketal B, and Bysspectin A
Brimble, Margaret A.,Davison, Emma K.,Shepperson, Caitlin E.,Wilson, Zoe E.
, p. 2345 - 2351 (2021)
The first total synthesis of the benzannulated 5,5-spiroketal natural products paeciloketal B and 1-epi-paeciloketal B has been achieved in 10 linear steps employing a biomimetic spiroketalization. This approach also furnished the related natural product
Evolution of N-Heterocycle-Substituted Iodoarenes (NHIAs) to Efficient Organocatalysts in Iodine(I/III)-Mediated Oxidative Transformations
Boelke, Andreas,Nachtsheim, Boris J.
supporting information, p. 184 - 191 (2019/12/11)
The reactivity of ortho-functionalized N-heterocycle-substituted iodoarenes (NHIAs) as organocatalysts in iodine(I/III)-mediated oxidations was systematically investigated in the α-tosyloxylation of ketones as the model reaction. During a systematic catalyst evolution, it was found that NH-triazoles and benzoxazoles have the most significant positive influence on the reactivity of the central iodine atom. A further catalyst improvement which focused on the substitution pattern of the arene revealed a remarkable ortho-effect. By introduction of an o-OMe group we were able to generate a novel NHIA with a so far unseen catalytic efficiency. This new catalyst is not only easy to synthesize but also enabled the α-tosyloxylation of carbonyl compounds at the lowest reported catalyst loading of only 1 mol%. Finally, the performance of this iodine(I) catalyst was successfully demonstrated in intramolecular oxidative couplings of biphenyls and oxidative rearrangements. (Figure presented.).
Catalytic Enantioselective Synthesis of Atropisomeric Biaryls: A Cation-Directed Nucleophilic Aromatic Substitution Reaction
Armstrong, Roly J.,Smith, Martin D.
, p. 12822 - 12826 (2016/02/18)
A catalytic enantioselective nucleophilic aromatic substitution reaction which yields axially chiral biaryl derivatives in excellent yields with e.r. values of up to 97:3 has been developed. This process uses a chiral counterion to direct the addition of thiophenolate to a prochiral dichloropyrimidine by a tandem desymmetrization/kinetic resolution mechanism. The products can be derivatized to a range of atropisomeric structures without any reduction in enantioenrichment, thus offering access to unexplored chiral biaryl architectures.
