IQUIR 05412
INSTITUTO DE QUIMICA ROSARIO
Unidad Ejecutora - UE
artículos
Título:
Second generation levoglucosenone-derived chiral auxiliaries.Scope and application in asymmetric Diels-Alder reactions
Autor/es:
SAROTTI, A.M.; SPANEVELLO, R.A.; SUÁREZ, A.G.
Revista:
TETRAHEDRON
Editorial:
ELSEVIER
Referencias:
Año: 2009 vol. 65 p. 3502 - 3508
ISSN:
0040-4020
Resumen:
Chiral alcohols were designed and easily prepared from levoglucosenone,a biomass-derived valuable synthon.These alcohols were tested as chiral auxiliaries in asymmetric Diels Alder reactions between the corresponding acrylates with acyclic and cyclic dienes.The regio,stereo,and facial selectivity varied from very good to excellent,depending upon the benzylic substitution of the auxiliary and the diene employed.As a consequence,after removal of the auxiliary,the resulting carboxylic acid derivatives were obtained in 72 99%ee.
