Pyrrolidine is one of the most frequently used aliphatic amines in medicinal chemistry: its residue can be found in at least ten FDA-approved drugs. Therefore, elaboration of practical synthetic approaches to novel substituted pyrrolidines is important. In this work, we synthesized a library of novel unique pyrrolidine building blocks using [3+2] cycloaddition between electron-deficient alkenes and azomethine ylides.1-4 Some synthesized structures are mimics of morpholine, β-proline derivatives, and fluorinated pyrrolidines. 1 V. Yarmolchuk et al. Tetrahedron 2014, 70, 3011. 2 V. Yarmolchuk et al. Eur. J. Org. Chem. 2013, 69, 3086. 3 V. Yarmolchuk et al. Tetrahedron Lett. 2011, 52, 1300. 4 V. Yarmolchuk et al. J. Org. Chem. 2011, 76, 7010.

Synthesis of novel unique pyrrolidines by [3+2]-cycloaddition of azomethine ylides with electron-deficient alkenes

251st National Meeting (2016)

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