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.
G. Cardillo; L. Gentilucci; E. Mosconi; A. Tolomelli; S. Troisi; E. Juaristi
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11585/98645
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