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EnglishA 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.
| Titolo: | Highly regio- and stereoselective palladium-catalyzed allylic carbonate amination. A practical route to dehydro-beta-amino esters | |
| Autore/i: | CARDILLO, GIULIANA; GENTILUCCI, LUCA; MOSCONI, ELISA; TOLOMELLI, ALESSANDRA; TROISI, STEFANO; E. Juaristi | |
| Autore/i Unibo: | ||
| Anno: | 2010 | |
| Rivista: | ||
| Digital Object Identifier (DOI): | http://dx.doi.org/10.1016/j.tet.2010.05.022 | |
| 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. | |
| Data prodotto definitivo in UGOV: | 2011-02-18 18:26:21 | |
| Appare nelle tipologie: | 1.01 Articolo in rivista |
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http://hdl.handle.net/11585/98645
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