Inherently Chiral Cavitand Curvature: Diastereoselective Oxidation of Tethered Allylsilanes

Inoue, Mami; Fujii, Yoshino; Matsumoto, Yasuhiro; Schramm, Michael; Iwasawa, Tetsuo

doi:10.1002/ejoc.201900891

Cited by 3 publications

(2 citation statements)

References 31 publications

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“…This state provides a binding pocket for supramolecular scientists to explore. Cavitands have a rich history of host-guest chemistry and now, with an inwardly directed coupled Au atom (1) [9], we have proposed that their potential to behave like biological catalysts will come to be [10][11][12][13].…”

Section: Introductionmentioning

confidence: 99%

Au-Cavitands: Size governed arene-alkyne cycloisomerization

Rusali

Schramm

2020

Tetrahedron Letters

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With an inwardly directed reactive center and a well-defined binding pocket, Au(I) functionalized resorcin[4]arene cavitands have been shown to catalyze molecular transformations. The reactivity profiles that emerge differ from other Au(I) catalysts. The added constraint of a binding pocket gives rise to the possibility that the substrates might have to fit into the resorcinarene pocket; our hypothesis is that substrates that match the available space have different reaction outcomes than those that do not. Herein we report on the intramolecular cyclization of alkyne-aromatic substrates with variable alkynes and aromatic composition. We see that scaffold size most drastically dictates reactivity, especially when the substrate's features are particularly designed. The results of these experiments add to the veritable goldmine of information about the selectivity in catalysis that cavitands offer.

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Section: Introductionmentioning

confidence: 99%

Au-Cavitands: Size governed arene-alkyne cycloisomerization

Rusali

Schramm

2020

Tetrahedron Letters

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“…Despite lower-symmetry resorcin[4]arenes and their cavitands featured in a number of reports, − only the C 4 -symmetric macrocycles are accessible in one step from non-macrocyclic precursors. A report of Mocerino and coworkers showed C 4 -symmetric derivatives 3 are easily prepared by the condensation of 3-methoxyphenol ( 1 ) with a range of aldehydes ( 2 , Scheme , pathway a).…”

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confidence: 99%

One-Step Synthesis of C_2v-Symmetric Resorcin[4]arene Tetraethers

et al. 2020

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The three-component reaction between a resorcinol, 1,3-dimethoxybenzene, and an alkyl aldehyde (R = C1–C11) along with BF3·OEt2 affords a C 2v-symmetric resorcin[4]arene tetraether in one step; in most cases, the single isomer can be precipitated from the reaction mixture in moderate to excellent yields (up to 89%). The reaction is tolerant of 2-substituted resorcinols (R′ = OH, Cl, Br, Me), allowing a third type of functionality to be regioselectively incorporated during the macrocyclization.

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