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.
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.File in questo prodotto:
Eventuali allegati, non sono esposti
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
