title: Spatially Directional Resorcin[4]arene Cavitand Glycoconjugates for Organic Catalysis.
abstract: The synthesis of novel spatially directional multivalent resorcin[4]arene cavitand glycoconjugates (RCGs) and their ability to catalyze organic reactions is reported. The β-d-glucopyranoside moieties on the upper rim of the "bowl"-shaped resorcin[4]arene cavitand core are capable of multiple hydrogen-bond interactions resulting in a pseudo-cavity, which has been investigated for organic transformations in aqueous media. The RCGs have been demonstrated to catalyze thiazole formation, thiocyanation, copper(I)-catalyzed azide alkyne cycloaddition (CuAAC), and Mannich reactions; they impart stereoselectivity in the three-component Mannich reaction. Thermodynamic values obtained from (1) H diffusion-ordered spectroscopy (DOSY) experiments suggest that the upper saccharide cavity of the RCG and not the resorcin[4]arene cavity is the site of the complexation event.
authors.affiliation: Department of Chemistry, University of South Florida, 4202 East Fowler Avenue, Tampa, Florida, 33620, USA.
authors.forename: Ali A
authors.initials: AA
authors.lastname: Husain
authors.affiliation: Department of Chemistry, University of South Florida, 4202 East Fowler Avenue, Tampa, Florida, 33620, USA.
authors.forename: Arthur M
authors.initials: AM
authors.lastname: Maknenko
authors.affiliation: Department of Chemistry, University of South Florida, 4202 East Fowler Avenue, Tampa, Florida, 33620, USA. kbisht@usf.edu.
authors.forename: Kirpal S
authors.identifier: http://orcid.org/0000-0003-1664-6343
authors.initials: KS
authors.lastname: Bisht
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D047250:Calixarenes / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D061565:Cycloaddition Reaction; D006001:Glycoconjugates / Q000737:chemistry*; D010649:Phenylalanine / Q000031:analogs & derivatives* / Q000737:chemistry; D013816:Thermodynamics
chemical_list: D000480:Alkynes; D001386:Azides; D006001:Glycoconjugates; C466160:resorcinarene; D047250:Calixarenes; D010649:Phenylalanine; D003300:Copper
keywords: cavitands; click chemistry; glycoconjugates; homogeneous catalysis; resorcin[4]arenes