Organic & Biomolecular Chemistry Blog

This week’s issue of OBC features art work from Qing Xu and Xin-Shan Ye et al.

Qing Xu and colleagues from Wenzhou University have developed a green copper catalyzed N-alkylation method for various amides and amines with alcohols, employing aerobic oxidation of the alcohols to aldehydes for a more effective way of activating the alcohols. This advantageous method uses a ligand-free catalyst and its only byproduct is water!

Copper-catalyzed N-alkylation of amides and amines with alcohols employing the aerobic relay race methodology
Qiang Li, Songjian Fan, Qing Sun, Haiwen Tian, Xiaochun Yu and Qing Xu
Org. Biomol. Chem., DOI: 10.1039/C1OB06743E

Xin-Shan Ye and co-workers at Peking University and University of Oxford have designed a concise route to a series of N-substituted ε-hexonolactams employing a tandem ring-expansion as the key step. These novel N-alkylated iminosugars are promising pharmacological chaperones for the treatment of N370S mutant Gaucher disease.

Synthesis of N-substituted ε-hexonolactams as pharmacological chaperones for the treatment of N370S mutant Gaucher disease
Guan-Nan Wang, Gabriele Twigg, Terry D. Butters, Siwei Zhang, Liangren Zhang, Li-He Zhang and Xin-Shan Ye
Org. Biomol. Chem., DOI: 10.1039/C2OB06987C

Both of these articles can be accessed for free for the next 6 weeks!

Other interesting articles in this issue are:

A perspective by Alfredo Ricci et al. about bioinspired organocatalytic asymmetric reactions

and 2 HOT articles which are free to access for the next 4 weeks:

Fluorimetric detection of Mg²⁺and DNA with 9-(alkoxyphenyl)benzo[b]quinolizinium derivatives
Maoqun Tian, Heiko Ihmels and Shite Ye
Org. Biomol. Chem., DOI: 10.1039/C2OB06948B

Substituted oxines inhibit endothelial cell proliferation and angiogenesis
Shridhar Bhat, Joong Sup Shim, Feiran Zhang, Curtis Robert Chong and Jun O. Liu
Org. Biomol. Chem., DOI: 10.1039/C2OB06978D

If you liked those why not view the rest of the issue HERE!

The cover of this week’s OBC features work from Min Shi et al. at Shanghai Institute of Organic Chemistry and Texas Tech University, who have used chiral zinc(II)–imidazoline–phosphine complexes in a novel catalytic system for the asymmetric Mannich-type difluorination of hydrazones with difluoroenoxysilanes.

Asymmetric catalytic Mannich-type reaction of hydrazones with difluoroenoxysilanes using imidazoline-anchored phosphine ligand–zinc(II) complexes
Zhiliang Yuan, Liangyong Mei, Yin Wei, Min Shi, Padmanabha V. Kattamuri, Patrick McDowell and Guigen Li
Org. Biomol. Chem., 2012, 10, 2509-2513
DOI: 10.1039/C2OB07022G

Read the full Communication; it is FREE to access for the next 6 weeks.

This issue also contains:

A Perspective review article: On a so-called “kinetic anomeric effect” in chemical glycosylation, by Ian Cumpstey

as well as the HOT article:

Synthesis and protein binding studies of a peptide fragment of clathrin assembly protein AP180 bearing an O-linked β-N-acetylglucosaminyl-6-phosphate modification
Mark E. Graham, Robin S. Stone, Phillip J. Robinson and Richard J. Payne

If you liked these why not have a look at the rest of the issue here