(S)-(+)-1-(2-pyrrolidinylmethyl)pyrrolidine – an effective catalyst of asymmetric synthesis

V. M. Tkachuk, V. M. Shoba, V. A. Sukach, M. V. Vovk

Abstract


The literature sources concerning application of 1-(pyrrolidin-2 ylmethyl)pyrrolidine as an effective organocatalyst of asymmetric reactions have been reviewed and systematized. The role of the tertiary amine fragment in the structure of the catalyst has been emphasized; it makes an asymmetric arrangement in the transition state of the key step during the new C-C bond formation. The importance of Bronsted acid as a promoter (additive), which protonates the basic nitrogen atom transforming it to the N-H-donor system, has been noted. Aldol condensation catalyzed by 1-(pyrrolidinyl-2-ylmethyl)pyrrolidine that can be undoubtedly considered as one the most valuable tools in asymmetric synthesis and construction of various optically active organic frameworks has been reviewed in details. A powerful catalytic activity of 1-(pyrrolidinyl-2-ylmethyl)pyrrolidine in the Mannich reaction leading to a new C-C bond and chiral centre creation has been demonstrated. A significant attention in the review is devoted to application of 1-(pyrrolidin-2-ylmethyl)pyrrolidine in the asymmetric version of the Mannich reaction as a convenient approach for the synthesis of chiral β-aminoketones and β-aminoesters being well known as useful building blocks and precursors for important nitrogen-containing natural products and heterocycles.


Keywords


asymmetric organocatalyst; (S)-(+)-1-(pyrrolidinylmethyl)-pyrrolidine; aldol condensation; Michael reaction, Mannich reaction (S)-(+)-1-(2-pyrrolidinylmethyl)pyrrolidine – an effective catalyst of asymmetric synthesis

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DOI: https://doi.org/10.24959/ophcj.14.784

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Abbreviated key title: Ž. org. farm. hìm.

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