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Springer (part of Springer Nature), Molecular Diversity, 2-4(7), p. 175-180

DOI: 10.1023/b:modi.0000006799.01924.2e

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Enhancing stereochemical diversity by means of microwave irradiation in the absence of solvent: Synthesis of highly substituted nitroproline esters via 1,3-dipolar reactions

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This paper is available in a repository.

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Abstract

Microwave irradiation induces the 1,3-dipolar cycloaddition of imines derived from alpha-aminoesters with beta-nitrostyrenes in the absence of solvent within 10-15 min. The reaction proceeds to give yields in the range 81-86% and three isomeric pyrrolidines are obtained in the cycloaddition. Consequently, the use of three imines and two beta-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.