IQUIR   05412
INSTITUTO DE QUIMICA ROSARIO
Unidad Ejecutora - UE
artículos
Título:
Highly diastereoselective Diels-Alder reaction using a chiral auxiliary derived from levoglucosenoone
Autor/es:
ARIEL M. SAROTTI, ROLANDO A. SPANEVELLO, ALEJANDRA G. SUÁREZ
Revista:
ORGANIC LETTERS
Editorial:
American Chemical Society
Referencias:
Lugar: Columbus; Año: 2006 vol. 8 p. 1487 - 1490
ISSN:
1523-7060
Resumen:
A new chiral auxiliary derived from levoglucosenone is reported. The compound is obtained by a cycloaddition reaction with 9-methoxy methylanthracene followed by a diastereoselective reduction of the C-2 keto function. The auxiliary has been used as chiral template in an asymmetric Diels-Alder reaction of the corresponding acrylic ester derivative with cyclopentadiene. The results showed excellent diastereomeric excess even at room temperature when the reaction is promoted by Et2AlCl as the Lewis acid.