Organic & Biomolecular Chemistry Blog

This Hot Article by Christopher Frost et al. at the University of Bath (UK) describes the utility of novel silyl-protected dioxaborinanes, performing as excellent donors in rhodium-catalysed 1,4-addition reactions under anhydrous conditions. This approach allows the enantioselective addition to arylidene Meldrum’s acid derivatives and a subsequent asymmetric synthesis of 4-arylchroman-2-ones, an important class of bioactive and pharmaceutically-relevant compounds.

Why not read this OBC Communication now! It will be FREE to access for the next four weeks.

Rhodium-catalysed enantioselective synthesis of 4-arylchroman-2-ones
Joseph C. Allen, Gabriele Kociok-Köhn and Christopher G. Frost
Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C1OB06586F, Communication

In this Hot Article, Alessandro Massi and colleagues at the University of Ferrara (Italy) disclose a novel approach to the Stetter reaction – the N-heterocyclic carbene (NHC)-catalyzed conjugate addition of acetyl anions to various α,β-unsaturated acceptors – in which 2,3-butandione (biacetyl) is used as an alternative surrogate of acetaldehyde.

We hope this new approach to NHC polarity reversal organocatalysis will catch your interest! You can read the article for FREE for the next 4 weeks.

Thiazolium-catalyzed intermolecular Stetter reaction of linear and cyclic alkyl α-diketones
Olga Bortolini, Giancarlo Fantin, Marco Fogagnolo, Pier Paolo Giovannini, Alessandro Massi and Salvatore Pacifico
Org. Biomol. Chem., 2011, Advance Article
DOI: 10.1039/C1OB06480K, Paper

The binding of two α-fucosylamide-based mimics of Lewis^X to DC-SIGN ECD (Dendritic Cell-Specific ICAM-3 Grabbing Nonintegrin extracellular domain) using STD NMR and docking studies has been investigated by Pedro M. Nieto and coworkers.  The mimics are shown to bind in a similar way to Lewis^X, through the fructose moiety and in a multi-modal fashion, but with increased affinity due to the aromatic moiety.

Insights into molecular recognition of Lewis^X mimics by DC-SIGN using NMR and molecular modelling
Cinzia Guzzi, Jesús Angulo, Fabio Doro, José J. Reina, Michel Thépaut, Franck Fieschi, Anna Bernardi, Javier Rojo and Pedro M. Nieto
Org. Biomol. Chem., 2011, 9, 7705-7712
DOI: 10.1039/C1OB05938F

Using DOSY NMR spectroscopy, collaborators from the Scripps Research Institute in La Jolla (USA) and Pfizer Worldwide Research have systemically measured the self-diffusion rates of linear vs. macrocyclic drug-like structures.

Check out this seminal work: selected as a HOT Article, it will free to access for the next 4 weeks*

Comparison of diffusion coefficients for matched pairs of macrocyclic and linear molecules over a drug-like molecular weight range
Andrew R. Bogdan, Nichola L. Davies and Keith James
Org. Biomol. Chem., 2011, 9, 7727-7733
DOI: 10.1039/C1OB05996C

* upon a simple registration process for individual access