Issue 35, 2022

Enamine-mediated Mannich reaction of cyclic N,O-acetals and amido acetals: the multigram synthesis of pyrrolidine alkaloid precursors

Abstract

The cooperative L-proline/Brønsted acid/base promoted reaction of 2-ethoxypyrrolidines or N-substituted 4,4-diethoxybutan-1-amines with methyl(alkyl/aryl)ketones for the synthesis of 2-(acylmethylene)pyrrolidine derivatives is reported. The key features of the developed protocol are gram-scale synthesis of the target compounds, easily available starting materials, operational simplicity and usage of non-expensive reagents.

Graphical abstract: Enamine-mediated Mannich reaction of cyclic N,O-acetals and amido acetals: the multigram synthesis of pyrrolidine alkaloid precursors

Supplementary files

Article information

Article type
Paper
Submitted
16 Jul 2022
Accepted
24 Aug 2022
First published
25 Aug 2022

Org. Biomol. Chem., 2022,20, 7105-7111

Enamine-mediated Mannich reaction of cyclic N,O-acetals and amido acetals: the multigram synthesis of pyrrolidine alkaloid precursors

R. A. Turmanov, A. V. Smolobochkin, A. S. Gazizov, T. S. Rizbayeva, D. D. Zapylkin, J. K. Voronina, A. D. Voloshina, V. V. Syakaev, A. V. Kurenkov, A. R. Burilov and M. A. Pudovik, Org. Biomol. Chem., 2022, 20, 7105 DOI: 10.1039/D2OB01276F

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