A pratical, highly enantioselective method for the synthesis of dehydro-beta-amino acids was developed starting from easily accessible enantiopure allylic carbonates.The substitution with amines for C-N bond formation on these substrates bearing substituents on the C-alpha,C-beta, and C-gamma position of the allylic system has received, until now, little attention. The reactions, carried out under palladium-catalyzed conditions, resulted in good yields and complete regioselectivity. Moreover, starting from enantiopure carbonates, complete retention of the configuration could be observed, affording enantiopure allylic amines.
G. Cardillo, L. Gentilucci, E. Mosconi, A. Tolomelli, S. Troisi, E. Juaristi (2010). Highly regio- and stereoselective palladium-catalyzed allylic carbonate amination. A practical route to dehydro-beta-amino esters. TETRAHEDRON, 66, 4994-4999 [10.1016/j.tet.2010.05.022].
Highly regio- and stereoselective palladium-catalyzed allylic carbonate amination. A practical route to dehydro-beta-amino esters
CARDILLO, GIULIANA;GENTILUCCI, LUCA;MOSCONI, ELISA;TOLOMELLI, ALESSANDRA;TROISI, STEFANO;
2010
Abstract
A pratical, highly enantioselective method for the synthesis of dehydro-beta-amino acids was developed starting from easily accessible enantiopure allylic carbonates.The substitution with amines for C-N bond formation on these substrates bearing substituents on the C-alpha,C-beta, and C-gamma position of the allylic system has received, until now, little attention. The reactions, carried out under palladium-catalyzed conditions, resulted in good yields and complete regioselectivity. Moreover, starting from enantiopure carbonates, complete retention of the configuration could be observed, affording enantiopure allylic amines.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
