Abstract
Microwave irradiation induces the 1,3-dipolar cycloaddition of imines derived from α-aminoesters with β-nitrostyrenesin the absence of solvent within 10–15 min. The reaction proceeds to give yields in the range 81–86% and three isomeric pyrrolidinesare obtained in the cycloaddition. Consequently, the use of three imines and two β-nitrostyrenes gives rise to a library of 18 nitroproline esters. The use of classical heating with longer reaction times (24 h) gives lower yields of products (below 50%) and only two stereoisomers can be detected in each reaction.
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Díaz-Ortiz, A., de la Hoz, A., Herrero, M.A. et al. Enhancing stereochemical diversity by means of microwave irradiation in the absence of solvent: Synthesis of highly substituted nitroproline esters via 1,3-dipolar reactions. Mol Divers 7, 175–180 (2003). https://doi.org/10.1023/B:MODI.0000006799.01924.2e
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DOI: https://doi.org/10.1023/B:MODI.0000006799.01924.2e