(S)-(+)-1-(2-піролідинілметил)піролідин – ефективний органокаталізатор асиметричного синтезу
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 arran...
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| Date: | 2014 |
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| Main Authors: | , , , |
| Format: | Article |
| Language: | Ukrainian |
| Published: |
National University of Pharmacy
2014
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| Subjects: | |
| Online Access: | https://ophcj.nuph.edu.ua/article/view/ophcj.14.784 |
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| Journal Title: | Journal of Organic and Pharmaceutical Chemistry |
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Journal of Organic and Pharmaceutical Chemistry| Summary: | 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. |
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