Host-guest complexation.  47.  Carcerands and carcaplexes, the first closed molecular container compounds

Cram, Donald J.; Karbach, Stefan; Kim, Young Hwan; Baczynskyj, L.; Marti, K.; Sampson, Russ M.; Kalleymeyn, G. W.

doi:10.1021/ja00216a031

Cited by 119 publications

(48 citation statements)

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“…Within his extensive studies in this field, Cram first synthesised carceplexes from bowl shaped cavitands; carceplexes are carcerands (hollow closed shell compounds) that encapsulate or rather trap guest molecules [38,39]. This inspired series of studies paved the way for future works into covalent organic capsules as reaction media, or into guest exchange in such assemblies for example, while unequivocally showing the presence of such incarcerated molecules by Fig.…”

Section: Covalent Organic Capsules/cages and Capsule-like Architecturesmentioning

confidence: 99%

Metallo-supramolecular capsules

Dalgarno

Power

Atwood

2008

Coordination Chemistry Reviews

534

216

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Section: Covalent Organic Capsules/cages and Capsule-like Architecturesmentioning

confidence: 99%

Metallo-supramolecular capsules

Dalgarno

Power

Atwood

2008

Coordination Chemistry Reviews

534

216

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“…28 The first synthetic cavitands only behaved as solvates embracing very small species like solvent molecules. 29 More recently, calix [5]arenes have been used as building blocks for the recognition of nonchiral larger molecules. 30 Chiral recognition has been attained very recently with molecular motifs based in resorcinanes in which a seam of hydrogen bonds in the upper rim of these systems maintains their concave shape (Fig.…”

Section: Molecular Vessels or Capsulesmentioning

confidence: 99%

Asymmetric induction under confinement

Brunet

2002

Chirality

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Confinement may efficiently condition the stereochemical outcome of a reaction through space constriction and molecular close contact. This article briefly reviews recent approaches of supramolecular chemistry to achieve chiral confinement. Crystallization is not always possible and the use of chiral crystals or clathrates lacks generality. The construction of solid supramolecular assemblies circumvents some of the problems of the crystal chemistry. In this regard, molecular imprinting of polymeric matrices with orifices mimicking the transition state of an enantioselective process is a very young, promising technique. Zeolites provide porous, rigid environments to host molecules without the need of lucky crystallizations, yet zeolites are not chiral per se and must be chirally modified. Besides, the limited dimension of their pores restricts the size of the guest molecules. Despite these problems, useful asymmetric photochemical reactions have been performed on zeolites. Finally, the formation of pillared lamellar structures, from inorganic salts of tetravalent transition metals covalently grafted with organic chains, is considered. The adequate selection of functionality and chirality of the organic pillars would afford custom-made, highly porous, 3D hybrid organo-inorganic scaffolds. However, the production of asymmetric processes within these layered materials still remains to be seen.

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“…19 The aryl bromide positions were further functionalized to the esters and subsequently reduced to give the tetrol cavitands. 20 Further functionization of the tetrol was conceived through a modular coupling approach using 2,2-bis(phenyldioxymethyl)propionic acid, 21 a well established synthetic building block in the synthesis of macromolecules. 22 However, this proved difficult, as we screened several DCC and DMAP mediated coupling, procedures.…”

Section: Resultsmentioning

confidence: 99%