Triflic acid-promoted post-Ugi condensation for the assembly of 2,6-diarylmorpholin-3-ones
Amire N. Almagambetova K.M. Turlykul A. Taishybay A. Nuroldayeva G. Belyaev A. Peshkov A.A. Utepbergenov D. Peshkov V.A.
16 October 2024Royal Society of Chemistry
Organic and Biomolecular Chemistry
2024#22Issue 489379 - 9387 pp.
We report a two-step one-pot synthesis of the 2,6-diarylmorpholin-3-one core based on the Ugi reaction of 2-oxoaldehyde with 2-hydroxycarboxylic acid, a primary amine and tert-butyl isocyanide followed by a triflic acid-promoted intramolecular condensation accompanied by the loss of the isocyanide-originated amide moiety. The overall transformation proceeds with complete retention of stereoconfiguration at the 2-hydroxycarboxylic acid-derived chiral center, allowing the target morpholin-3-ones to be obtained in an enantiopure form. Subsequent double bond hydrogenation and amide reduction allow the degree of unsaturation to be reduced, providing a convenient entry to the cis-2,6-diphenylmorpholine motif.
Text of the article Перейти на текст статьи
Department of Chemistry, School of Sciences and Humanities, Nazarbayev University, Astana, 010000, Kazakhstan
Department of Chemistry, University of Jyväskylä, FI-40014, Finland
Department of Chemistry, University of Eastern Finl, Joensuu, FI-80101, Finland
Department of Chemistry
Department of Chemistry
Department of Chemistry
10 лет помогаем публиковать статьи Международный издатель
Книга Публикация научной статьи Волощук 2026 Book Publication of a scientific article 2026