A simple and efficient method for C-2 deuterium labeling of 3,4-di-tert-butoxypyrroline N-oxide, a useful chiral building block in azaheterocycles syntheses, is presented. Selective and quantitative deuterium incorporation (> 99 %) was achieved by base-catalyzed H/D exchange in D2O under mild reaction conditions. A mechanistic pathway based on kinetic and computational data was proposed. The labeled nitrone was used in the synthesis of C-8a deuterated (1R,2R,8aR)-lentiginosine.
Regioselective Deuteration of a 3,4-Dialkoxypyrroline N-Oxide and Synthesis of 8a-d-Indolizidines / Ranzenigo, Anna; Mercurio, Chiara; Karrenbrock, Maurice; Cordero, Franca M.; Cardini, Gianni; Pagliai, Marco; Brandi, Alberto. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1099-0690. - STAMPA. - (2020), pp. 3423-3429. [10.1002/ejoc.202000402]
Regioselective Deuteration of a 3,4-Dialkoxypyrroline N-Oxide and Synthesis of 8a-d-Indolizidines
Ranzenigo, Anna;Cordero, Franca M.
;Cardini, Gianni;Pagliai, Marco;Brandi, Alberto
2020
Abstract
A simple and efficient method for C-2 deuterium labeling of 3,4-di-tert-butoxypyrroline N-oxide, a useful chiral building block in azaheterocycles syntheses, is presented. Selective and quantitative deuterium incorporation (> 99 %) was achieved by base-catalyzed H/D exchange in D2O under mild reaction conditions. A mechanistic pathway based on kinetic and computational data was proposed. The labeled nitrone was used in the synthesis of C-8a deuterated (1R,2R,8aR)-lentiginosine.I documenti in FLORE sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.