A novel design of a levoglucosenone derived chiral auxiliary

SAROTTI, A.M.; SPANEVELLO, R.A.; SUÁREZ, A.G.

TETRAHEDRON LETTERS

ELSEVIER

Año: 2004 vol. 45 p. 8203 - 8206

0040-4039

A two-step general approach to a new chiral auxiliary starting from levoglucosenone is reported. The compound is obtained by a [4+2] cycloaddition reaction with anthracene followed by a diastereoselective reduction of the C-2 keto function in high overall yield. The auxiliary has been used as chiral template in an asymmetric Diels–Alder reaction of the corresponding acrylic ester derivative with cyclopentadiene and shown to be efficient for asymmetric induction.