Second generation Levoglucosenone-derived chiral auxiliaries. Scope and application in asymmetric Diels-Alder reactions.

ARIEL M. SAROTTI; ROLANDO A. SPANEVELLO; ALEJANDRA G. SUÁREZ

TETRAHEDRON

PERGAMON-ELSEVIER SCIENCE LTD

Año: 2009 vol. 65 p. 3502 - 3508

0040-4020

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 correspondig 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 carbosylic acid derivatives were obtained in 72-99% ee.