From Waste Paper to a Chiral Auxiliary

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

VENECIA, ITALIA

Otro; Sixth Summer School on Green Chemistry; 2003

Paper is an important industrial material for modern civilization and it is used in a wide variety of applications. An increasing demand of this material has forced the use of waste paper as a source of new paper and paper-board products. By doing this, great energy saving can be achieved and less wood from the forest is needed. Eventhough recycling techniques have been improved since World War II, the process has some drawbacks: recycled paper is not as good as the original one and there is a limit to the number of times a piece of paper can be recycled. Since more than 20 % of municipal waste in modern society is constituted by cellulosic material, it is evident that those alternatives which allow the conversion of waste paper into high value products are not only interesting but also necessary.Levoglucosenone 1 is a member of the carbohydrate chiral pool. This a,b-unsaturated bicyclic ketone can be obtained from acid pyrolisis of cellulose or cellulose containing material, like waste paper, Scheme 1. This enantiomeric pure heterocyclic structure has been used as starting material in the synthesis of different natural products, however, it has never been employed as a chiral inductor.