A NOVEL SYNTHESIS OF DIDEHYDROAMINO ACID-ESTERS FROM AZOMETHINE YLIDES

Authors
GROUNDWATER PW SHARIF T ARANY A HIBBS DE HURSTHOUSE MB GARNETT I NYERGES M
Citation
Pw. Groundwater et al., A NOVEL SYNTHESIS OF DIDEHYDROAMINO ACID-ESTERS FROM AZOMETHINE YLIDES, Journal of the Chemical Society. Perkin transactions. I (Print), (17), 1998, pp. 2837-2846
Citations number
34
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I (Print) → ACNP
ISSN journal
0300922X
Issue
17
Year of publication
1998
Pages
2837 - 2846
Database
ISI
SICI code
0300-922X(1998):17<2837:ANSODA>2.0.ZU;2-L
Abstract
A novel synthesis of didehydroamino acid (DDAA) esters 5 is described, starting from aldimines 2. The mechanism for this reaction has been s hown to involve the cycloaddition of an azomethine ylide 3 to an Imine 2, followed by the base-catalysed ring-opening of the resulting imida zolidine intermediate 7. This novel method has also been extended to t he synthesis of DDAA esters 5 catalysed by imines.