Results, a Proposed von Hippel-Lindau (VHL) Degrader Gene ID reaction mechanism for this one-pot reaction is illustrated in Scheme four, which consists of the sequence of aminochlorination, aziridination and followed by the S N two nucleophilic ring-opening. The initial step could be the Cu-catalyzed aminochlorination reaction of methyl cinnamate 1a resulting in anti-chloroamine intermediate A. The secondBeilstein J. Org. Chem. 2014, 10, 1802807.affording the target merchandise in good-to-excellent chemical yields. Furthermore, this reaction provides practically full stereochemical outcomes, and only the anti-isomer is discovered for all the instances, which offers an easy access to ,-diamino acid derivatives.Scheme 3: Ring-opening of aziridine 6.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 (three.0 mL). The reaction vial was loaded with freshly activated four molecular sieves (250 mg), TsNCl2 (1.0 mmol) and Cu(OTf)two (10 mol ). The answer in the capped vial was stirred at room temperature for 24 h with no argon protection. The reaction was ultimately quenched by dropwise addition of saturated aqueous Na2SO3 resolution (3.0 mL). After quench for 30 min, benzylamine (2.0 mL) was added towards the mixture exposed to air. Another one hour was required till conversion was complete. Then the phases were separated, and the aqueous phase was extracted with ethyl acetate (three 10 mL). The MMP-9 Activator Purity & Documentation combined organic layers have been 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) offered final goods five.step involves a common intramolecular SN2 substitution reaction of intermediate A with the aid of benzylamine, to give the aziridine intermediate B. The intermediate B undergoes a S N two nucleophilic method attacked by benzylamine, major to the formation with the final item 5a. The exceptional stereoselectivity and formation of only anti-isomer is often explained by the formation of aziridine intermediate and complete geometry manage with the following SN2 nucleophilic attack. The formation on the unexpected diamino ester, as an alternative to aziridine, might be due to the relative robust nucleophilicity of benzylamine. Taking into consideration the fact that the final solution 5a is anti plus the aminohalogenation product intermediate A can also be anti, the only approach to clarify the stereochemistry of item five would be the double inversion via aziridine formation. The direct substitution from the Cl atom is achievable, nevertheless it will lead to the syn product 5. For that reason we think that the interpretation in the observed stereochemical outcome will have to involve the intermediate aziridine formation.Supporting InformationSupporting Info FileExperimental details and spectral information. [ supplementary/1860-5397-10-189-S1.pdf]ConclusionIn conclusion, a new one-pot approach for the synthesis of ,differentiated diamino esters straight from ,-unsaturated esters has been developed. The reaction sequence contains copper-catalyzed aminochlorination, aziridination and S N two nucleophilic ring-opening reaction. This one-pot reaction is operationally practical and can tolerate various substratesAcknowledgementsWe gratefully acknowledge the financial support in the National Organic Science Foundation of China (No. 21102071)Scheme 4: Proposed mechanism.Beilstein J. Org. Chem. 2014, ten, the Basic Research Funds.