Cellulose as source of new chiral inductors for asymmetric synthesis

MARÍA C. BOTTA; VALERIA CORNE; DAVID F. LLOMPART; MARÍA M. ZANARDI; ARIEL M. SAROTTI; ALEJANDRA G. SUÁREZ; ROLANDO A. SPANEVELLO

Montreal

Otro; 9th Annual ACS Summer School on Sustainability on Green Chemistry; 2011

American Chemical Society

We have developed new chiral auxiliaries and catalysts in a simple and efficient way derived from levoglucosenone, the major product of the pyrolysis of cellulose containing materials. The amino alcohols demonstrated 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. These results, in addition to the fact that the starting material is inexpensive,make these systems excellent models to be further employed in other asymmetric reactions.