(S)-(+)-1-(2-піролідинілметил)піролідин – ефективний органокаталізатор асиметричного синтезу

• Дата: 2014
• Автори: Tkachuk, V. M., Shoba, V. M., Sukach, V. A., Vovk, M. V.
• Формат: Стаття
• Мова: Ukrainian
• Опубліковано: National University of Pharmacy 2014
• Теми: асиметричний органокаталіз; 2-(S)-( )-1-(2-піролідинілметил)піролідин; альдольна конденсація; реакції Міхаеля та Манніха; УДК 547.744 544.473 544.122.3
• Онлайн доступ: https://ophcj.nuph.edu.ua/article/view/ophcj.14.784
• Назва журналу: Journal of Organic and Pharmaceutical Chemistry

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.