Innovative transformation of cellulosic materials into useful chemicals

GIORDANO, E. D.; BOTTA, M. C.; CORNE, V.; GIRI, G. F.; LLOMPART, D. F.; MANGIONE, M. I.; SAROTTI, A. M.; SUÁREZ, A. G.; SPANEVELLO, R. A.

Golden

Otro; ACS Summer School on Green Chemistry and Sustainable Energy; 2012

American Chemical Society

Levoglucosenone has proven to be an important synthon for the development of chiral amplification, chiral auxiliaries and chiral catalysts. In this work we have synthetised tri-O-acetyl-D-allal in six steps with 56% overall yield from levoglucosenone. This new procedure for the preparation of subtituted D-allal demostrated to be simple and efficient. The amino alcohols showed to be efficient catalysts for the enantioselective alkylation of benzaldehyde with diethylzinc. The chiral auxiliaries have shown to be excellent inductors in asymmetric Diels-Alder reactions.