Directed Ortho Metallation of Deep Cavity Cavitands: Functionalizing Molecular Concavity
- 12 October 2005
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 71 (4) , 1289-1294
- https://doi.org/10.1021/jo0513515
Abstract
Directed ortho metallation (DOM) processes have been used to functionalize the cavity and rim of title cavitand 1. The preorganization of the host resulted in a considerable reduction in the range of products produced. Thus, whereas sixty-nine products are possible from per-functionalization, only twelve were observed when the host was treated with three different alkyllithiums.Keywords
This publication has 24 references indexed in Scilit:
- The 2×3 Toolbox of Organometallic Methods for Regiochemically Exhaustive FunctionalizationAngewandte Chemie International Edition in English, 2004
- A Functionalized, Deep Cavitand Catalyzes the Aminolysis of a Choline DerivativeJournal of the American Chemical Society, 2004
- A Novel C3v-Symmetrical Calix[6](aza)cryptand with a Remarkably High and Selective Affinity for Small AmmoniumsThe Journal of Organic Chemistry, 2004
- Reactivity and Molecular Recognition: Amine Methylation by an Introverted EsterJournal of the American Chemical Society, 2003
- Capped CyclodextrinsChemical Reviews, 2003
- First C3v-Symmetrical Calix[6](aza)crownThe Journal of Organic Chemistry, 2003
- Guest Binding and Orientation within Open Nanoscale HostsChemistry – A European Journal, 2002
- Calix[6]arene-Based Cuprous “Funnel Complexes”: A Mimic for the Substrate Access Channel to Metalloenzyme Active SitesJournal of the American Chemical Society, 2002
- Cavitand−PorphyrinsJournal of the American Chemical Society, 2001
- Enzyme modelsRecueil des Travaux Chimiques des Pays-Bas, 1994