Results, a proposed reaction mechanism for this one-pot reaction is illustrated in Scheme 4, which consists of the sequence of aminochlorination, aziridination and followed by the S N two nucleophilic ring-opening. The initial step is the Cu-catalyzed aminochlorination reaction of methyl cinnamate 1a mGluR1 Activator Storage & Stability resulting in anti-chloroamine intermediate A. The secondBeilstein J. Org. Chem. 2014, 10, 1802807.affording the target products in good-to-excellent chemical yields. In addition, this reaction offers virtually full stereochemical outcomes, and only the anti-isomer is found for each of the situations, which offers a simple access to ,-diamino acid derivatives.Scheme three: Ring-opening of aziridine six.ExperimentalGeneral process for the one-pot synthesis of ,-diamino esters: Into a dry vial was added cinnamic ester 4 (0.50 mmol) and freshly distilled acetonitrile (3.0 mL). The reaction vial was loaded with freshly activated 4 molecular sieves (250 mg), TsNCl2 (1.0 mmol) and Cu(OTf)two (10 mol ). The solution within the capped vial was stirred at space temperature for 24 h with no argon protection. The reaction was lastly quenched by dropwise addition of saturated aqueous Na2SO3 option (3.0 mL). After quench for 30 min, benzylamine (two.0 mL) was added towards the mixture exposed to air. Yet another one particular hour was required until conversion was comprehensive. Then the phases have been separated, and also the aqueous phase was extracted with ethyl acetate (three 10 mL). The combined organic layers were washed with brine, dried more than anhydrous sodium sulfate, and concentrated to dryness. Purification by flash chromatography (EtOAc/hexane, from 1:20 to 1:3, v/v) provided final items 5.step requires a typical intramolecular SN2 substitution reaction of intermediate A using the help of benzylamine, to provide the aziridine intermediate B. The intermediate B undergoes a S N two nucleophilic method attacked by benzylamine, major for the formation from the final item 5a. The excellent stereoselectivity and formation of only anti-isomer is Phospholipase A Inhibitor Storage & Stability usually explained by the formation of aziridine intermediate and comprehensive geometry control in the following SN2 nucleophilic attack. The formation with the unexpected diamino ester, instead of aziridine, may very well be due to the relative robust nucleophilicity of benzylamine. Thinking about the truth that the final product 5a is anti along with the aminohalogenation product intermediate A is also anti, the only method to explain the stereochemistry of solution five is definitely the double inversion by means of aziridine formation. The direct substitution of your Cl atom is achievable, however it will bring about the syn product 5. As a result we think that the interpretation of your observed stereochemical outcome will have to involve the intermediate aziridine formation.Supporting InformationSupporting Facts FileExperimental particulars and spectral information. [ supplementary/1860-5397-10-189-S1.pdf]ConclusionIn conclusion, a new one-pot method for the synthesis of ,differentiated diamino esters straight from ,-unsaturated esters has been created. The reaction sequence includes copper-catalyzed aminochlorination, aziridination and S N two nucleophilic ring-opening reaction. This one-pot reaction is operationally easy and can tolerate a variety of substratesAcknowledgementsWe gratefully acknowledge the economic help from the National All-natural Science Foundation of China (No. 21102071)Scheme four: Proposed mechanism.Beilstein J. Org. Chem. 2014, 10, 1802807.and also the Basic Study Funds.