Stereoselective Total Synthesis of 1,4-Dideoxy-1,4-imino-L-ribitol by an Intramolecular Ring Opening of Epoxide with a Tethered Amide

Stereoselective total synthesis of 1,4-dideoxy-1,4-imino-L-ribitol has been accomplished from D-glucose. The key step involved in this synthesis is the regioselective ring-opening of the epoxide with a tethered amido group to give the N-tosyl-3,6-dideoxy-3,6-imino-1,2- O-isopropylidene-α-D-glucofuranose.

Metal-free Deamidative Ugi Access to Isoindolinones

A two-step isoindolone synthesis has been achieved by using an Ugi/oxidative vicarious nucleophilic substitution sequence starting from 3-nitrobenzoic acid and aromatic aldehydes. Loss of the amido group was observed as well as a further oxidative process towards hydroxyisoindolone derivatives after prolonged stirring open to the atmosphere.

Stereoselective Allylation of Linear and Chiral β-Amino-α-Hydroxy Aldehydes: Total Syntheses of Tetraacetyl d-lyxo-, d-ribo-, and d-arabino-Phytosphingosines

The stereoselective allylations of β-amino-α-hydroxy aldehydes­ are described. Several Lewis acids (BF3·OEt2, SnCl4, TiCl4, ZnCl2­, and MgBr2·OEt2) were utilized in the allylations. The allylation of anti-β-NHCbz-α-OTBS substrate mediated by SnCl4 afforded the syn-selective­ product, while its allylation mediated by BF3·OEt2 afforded the anti-selective product. The allylation of syn-β-NHCbz-α-OTBS mediated by SnCl4 afforded the anti-selective product. The mechanism involves the chelation between the amido group and aldehyde oxygen by SnCl4, and the Felkin–Anh model by BF3·OEt2. The resulting allylation products were used for the total syntheses of tetraacetyl d-lyxo-, d-ribo-, and d-arabino-phytosphingosines.

Tunable intramolecular H-bonding promotes benzoic acid activity in polymerization: inspiration from nature

Intramolecular H-bonding of ortho-amido group(s) tuned benzoic acid into strong Brønsted acid active in ring-opening polymerizations of lactones and trimethylene carbonate at room temperature in solutions.

Potent triazine-based dehydrocondensing reagents substituted by an amido group

This study describes the synthesis of triazine-based dehydrocondensing reagents substituted by amido substituents and demonstrates their efficiency for dehydrocondensing reactions in MeOH and THF. N-Phenylbenzamido-substituted chlorotriazine is readily converted to a stable, non-hygroscopic triazinylammonium-based dehydrocondensing reagent that is superior to 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM) in terms of its reactivity in dehydrocondensing reactions.