A simple strategy for the synthesis of hydroxyethylene dipeptide isostere from D-glucose

Formation of Scalemic Aziridines via the Nucleophilic Opening of Aziridines

“…Our plan (Scheme ) was to prepare the aziridine 2 and to examine the reactivity of this molecule with a variety of organometallic reagents. The reaction of the aziridine ring with cuprates, organolithium reagents, and Grignard reagents is well known . We were not certain where nucleophilic attack would take place with an aziridine such as 2 , and a variety of products are possible.…”

Synthesis of Fingolimod Employing Regioselective Aziridine Ring-Opening Reaction as a Key Step

“…Regioselective aziridine ring opening could be exemplified by a reaction with cuprates R 2 CuLi in the presence of BF 3 ·Et 2 O, providing corresponding secondary amines . An even more exciting possibility is the aziridine ring opening using Grignard reagents in the presence of Cu­(I) catalysts, which is also documented in the literature. − A similar reaction involving protected aziridine spiro compounds was used by Hong et al for desymmetrization of 2-substituted serinols also using the aziridine 5a (Figure ). …”

“…The organic phase, after evaporation, was purified by column chromatography (silica gel, 2−10 vol % of EtOAc in hexanes), yielding 351 mg (53%) of the product 20. 1,2-Bis(4-octylphenyl)ethane (21). A flask equipped with a magnetic stir bar and a reflux condenser was charged with 385 mg of magnesium (15.8 mmol, 0.55 equiv), 15 mL of dry THF, and 50 μL of 1,2-dibromoethane (5 mol % to Mg).…”