Cetate (three ten mL). The combined organic H2 Receptor site layers had been washed with brine, dried
Cetate (3 ten mL). The combined organic layers were washed with brine, dried more than anhydrous sodium sulfate, and concentrated to dryness. Purification by flash chromatography (EtOAchexane, from 1:20 to 1:three, vv) supplied final merchandise five.step requires a typical intramolecular SN2 substitution reaction of intermediate A together with the help of benzylamine, to offer the aziridine intermediate B. The intermediate B undergoes a S N 2 nucleophilic course of action attacked by benzylamine, top for the formation from the final item 5a. The outstanding stereoselectivity and formation of only anti-isomer might be explained by the formation of aziridine intermediate and full geometry handle in the following SN2 nucleophilic attack. The formation in the unexpected diamino ester, as an alternative of aziridine, can be on account of the relative strong nucleophilicity of benzylamine. Thinking about the truth that the final product 5a is anti along with the aminohalogenation item intermediate A is also anti, the only solution to explain the stereochemistry of product 5 is the double inversion by means of aziridine formation. The direct substitution with the Cl atom is probable, however it will bring about the syn solution 5. Therefore we believe that the interpretation of your observed stereochemical outcome need to involve the intermediate aziridine formation.Supporting InformationSupporting Facts FileExperimental information and spectral data. [http:beilstein-journals.orgbjoccontent supplementary1860-5397-10-189-S1.pdf]ConclusionIn conclusion, a brand new one-pot process for the synthesis of ,differentiated diamino esters directly from ,-unsaturated esters has been created. The reaction sequence includes copper-catalyzed aminochlorination, aziridination and S N 2 nucleophilic ring-opening reaction. This one-pot reaction is operationally hassle-free and may tolerate a variety of substratesAcknowledgementsWe gratefully acknowledge the economic assistance from the National All-natural Science Foundation of China (No. 21102071)Scheme four: Proposed mechanism.Beilstein J. Org. Chem. 2014, 10, 1802807.along with the Fundamental Investigation Funds for the Central Universities (No. 1107020522 and No. 1082020502). The Jiangsu 333 system (for Pan) and Changzhou Jin-Feng-Huang plan (for Han) are also acknowledged.22. Soloshonok, V. A.; Ohkura, H.; Sorochinsky, A.; Voloshin, N.; Markovsky, A.; Belik, M.; Yamazaki, T. Tetrahedron Lett. 2002, 43, 5445448. doi:ten.1016S0040-4039(02)01103-6 23. de Figueiredo, R. M. Angew. Chem., Int. Ed. 2009, 48, 1190193. doi:10.1002anie.200804362 24. Du, H.; Zhao, B.; Shi, Y. J. Am. Chem. Soc. 2007, 129, 76263. doi:10.1021ja0680562 25. Mu z, K.; Nieger, M. Chem. Commun. 2005, 2729731. doi:10.1039B502150B 26. Li, G.; Kim, S. H.; Wei, H.-X. Tetrahedron Lett. 2000, 41, 8699703. doi:10.1016S0040-4039(00)KDM4 Storage & Stability 01579-3 27. Li, G.; Wei, H.-X.; Kim, S. H.; Carducci, M. D. Angew. Chem., Int. Ed. 2001, 40, 4277280. doi:ten.10021521-3773(20011119)40:224277::AID-ANIE42773.0.CO ;2-I 28. Wu, H.; Ji, X.; Sun, H.; An, G.; Han, J.; Li, G.; Pan, Y. Tetrahedron 2010, 66, 4555559. doi:10.1016j.tet.2010.04.054 29. Li, G.; Saibabu Kotti, S. R. S.; Timmons, C. Eur. J. Org. Chem. 2007, 2745758. doi:ten.1002ejoc.200600990 See to get a assessment on aminohalogenation. 30. Han, J.-L.; Zhi, S.-J.; Wang, L.-Y.; Pan, Y.; Li, G. Eur. J. Org. Chem. 2007, 1332337. doi:ten.1002ejoc.200600902 31. Mei, H.; Han, J.; Li, G.; Pan, Y. RSC Adv. 2011, 1, 42933. doi:ten.1039c1ra00174d 32. Li, G.; Wei, H.-X.; Kim, S. H.; Neighbors, M. Org. Lett. 1999, 1, 39598. doi:10.1021ol99.