Asian Journal of Organic Chemistry

No foul: Poly(oligo(ethylene glycol) methacrylate) (pOEGMA) was grafted onto a cyclic olefin copolymer (COC) surface by photografting of a perfluoroaryl azide-based initiator and surface-initiated, atom-transfer radical polymerization. The pOEGMA was then spatioselectively functionalized to generate a biotin-streptavidin micropattern.

Being the alpha: Despite the synthetic utility of chiral alkyl chlorides, catalytic methods for achieving enantioselective chlorination were only developed a decade ago. This Focus Review discusses the catalytic enantioselective α-chlorination of carbonyl compounds, as well as some stereospecific substitution reactions of the resulting optically active chlorides.

Efficiency and economics matter: 5,5-dimethyl-1,3-dibromohydantoin is an efficient and economical reagent for the bromination of 1,4,5,8-naphthalenetetracarboxylic dianhydride. Bromination is achieved under mild reaction conditions and the products are isolated by recrystallization. The utility of the bromo derivatives is demonstrated by converting them into imide and core-substituted naphthalene diimides, which have tunable electronic and optical properties.

High on selectivity: β-Isocupreidine catalyzes the formation of enantiomerically enriched, 3-substituted 3-hydroxyoxindole derivatives in an enantioselective Morita–Baylis–Hillman reaction of maleimides with isatin derivatives. The products are obtained in up to 96 % yield and enantiomeric excesses of over 99 % ee are achieved under mild reaction conditions.

Vitamin B₁₂ - more possibilities: An efficient method for the aminolysis of cobyrinic acid derivatives catalyzed by a benzotriazole/DBU system is described. The synthesized cobinamide derivatives can be easily functionalized at either the c or meso position. (CN)₂Cby(III)OMe₇ is prone to hydroxylation at the C8 position. The location of hydroxylation was confirmed through NMR analysis and the reactivity of this position was analyzed by computational methods.